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CAS No. : | 64224-21-1 | MDL No. : | |
Formula : | C8H6N2S3 | Boiling Point : | - |
Linear Structure Formula : | - | InChI Key : | CKNAQFVBEHDJQV-UHFFFAOYSA-N |
M.W : | 226.34 | Pubchem ID : | 47318 |
Synonyms : |
RP 35972;NSC 347901;CD1400
|
Num. heavy atoms : | 13 |
Num. arom. heavy atoms : | 11 |
Fraction Csp3 : | 0.12 |
Num. rotatable bonds : | 1 |
Num. H-bond acceptors : | 2.0 |
Num. H-bond donors : | 0.0 |
Molar Refractivity : | 59.02 |
TPSA : | 114.35 Ų |
GI absorption : | High |
BBB permeant : | No |
P-gp substrate : | No |
CYP1A2 inhibitor : | Yes |
CYP2C19 inhibitor : | No |
CYP2C9 inhibitor : | No |
CYP2D6 inhibitor : | No |
CYP3A4 inhibitor : | No |
Log Kp (skin permeation) : | -6.92 cm/s |
Log Po/w (iLOGP) : | 1.88 |
Log Po/w (XLOGP3) : | 1.07 |
Log Po/w (WLOGP) : | 3.3 |
Log Po/w (MLOGP) : | 0.25 |
Log Po/w (SILICOS-IT) : | 5.83 |
Consensus Log Po/w : | 2.47 |
Lipinski : | 0.0 |
Ghose : | None |
Veber : | 0.0 |
Egan : | 0.0 |
Muegge : | 0.0 |
Bioavailability Score : | 0.55 |
Log S (ESOL) : | -2.48 |
Solubility : | 0.754 mg/ml ; 0.00333 mol/l |
Class : | Soluble |
Log S (Ali) : | -3.06 |
Solubility : | 0.196 mg/ml ; 0.000865 mol/l |
Class : | Soluble |
Log S (SILICOS-IT) : | -3.63 |
Solubility : | 0.0529 mg/ml ; 0.000234 mol/l |
Class : | Soluble |
PAINS : | 0.0 alert |
Brenk : | 1.0 alert |
Leadlikeness : | 1.0 |
Synthetic accessibility : | 3.14 |
Signal Word: | Warning | Class: | N/A |
Precautionary Statements: | P261-P305+P351+P338 | UN#: | N/A |
Hazard Statements: | H315-H319-H335 | Packing Group: | N/A |
GHS Pictogram: |
* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With tetraphosphorus decasulfide In 5,5-dimethyl-1,3-cyclohexadiene; toluene at 135℃; for 4 h; | General procedure: P4S10 (12 g, 27.0 mmol), toluene (90 ml) and xylene (90 ml)were added to a reactor and heated to a temperature of 120 C.Compound 5a (8.1 g, 45.1 mmol) was added to the reactor. Thereaction mixture was allowed to proceed under reflux at 135 Cfor 4 h and then cooled to 20 C and filtered through Celite. The solventwas then removed under reduced pressure and the resultantred solid was extracted with CH2Cl2. The organic layer was washedwith aqueous K2CO3 solution, dried over Na2SO4, and filtered. Thesolvent was removed under reduced pressure and the crude solidwas dried in vacuo. The dried solid was washed with cold EtOAc,and then recrystallized in acetonitrile to give 1a (0.9 g, 10percent) as ared solid. |
13.6% | With phosphorous (V) sulfide In toluene; xylene at 135℃; for 4 h; | Example 3; Synthesis and recrystallization of oltipraz. 300 mL of toluene, 350 mL of xylene, and 48.0 g (216 mmole) of phosphorus pentasulfide were added to a reactor and heated to a temperature of 120 to 122°C. 40.0 g (206 mmole) of methyl 2-metbyl-3-(pyrazin-2-yl)-3-oxopropionate prepared in Example 2 was dissolved in 100 mL of toluene and then dropwise added to the reactor. The reaction solution was allowed to proceed under reflux at 135°C for 4 hours and then cooled to 20 C. After addition of 500 mL of distilled water and 500 mL of methanol, the pH of the resultant reaction solution was adjusted to 8.5 with adding a 28percent ammonia solution (about 51 mL). An organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. 150 mL of methanol was added to the resultant concentrate, stirred for one hour, and filtered. A filtrate was washed with 100 mL of methanol to give a humid oltipraz crude crystal (12.0 to 13.0 g). The oltipraz crude crystal was placed in a reactor. 400 mL of acetonitrile was added and dissolved at 80 °C. 1.4 g of activated carbon was added and stirred for 30 minutes. The resultant solution was filtered, washed with 100 mL of acetonitrile, crystallized with stirring at a temperature of 20 to 25°C for 2 hours, and again stirred at 10°C for one hour. The obtained crystal was filtered, washed with 20 mL of acetonitrile, and vacuum dried at 40 °C to give 6.37 g of oltipraz (13.6percent yield, >99.5percent purity). NMR (6 CDC13) : 2.51 (s, 3H), 8.70 (d, 1H), 8.80 (d, 1H), 9.21 (s, 1H) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
14% | With tetraphosphorus decasulfide; In 5,5-dimethyl-1,3-cyclohexadiene; toluene; at 135℃; for 4h; | General procedure: P4S10 (12 g, 27.0 mmol), toluene (90 ml) and xylene (90 ml)were added to a reactor and heated to a temperature of 120 C.Compound 5a (8.1 g, 45.1 mmol) was added to the reactor. Thereaction mixture was allowed to proceed under reflux at 135 Cfor 4 h and then cooled to 20 C and filtered through Celite. The solventwas then removed under reduced pressure and the resultantred solid was extracted with CH2Cl2. The organic layer was washedwith aqueous K2CO3 solution, dried over Na2SO4, and filtered. Thesolvent was removed under reduced pressure and the crude solidwas dried in vacuo. The dried solid was washed with cold EtOAc,and then recrystallized in acetonitrile to give 1a (0.9 g, 10percent) as ared solid. |
13.6% | With phosphorous (V) sulfide; In toluene; xylene; at 135℃; for 4h; | Example 3; Synthesis and recrystallization of oltipraz. 300 mL of toluene, 350 mL of xylene, and 48.0 g (216 mmole) of phosphorus pentasulfide were added to a reactor and heated to a temperature of 120 to 122°C. 40.0 g (206 mmole) of methyl 2-metbyl-3-(pyrazin-2-yl)-3-oxopropionate prepared in Example 2 was dissolved in 100 mL of toluene and then dropwise added to the reactor. The reaction solution was allowed to proceed under reflux at 135°C for 4 hours and then cooled to 20 C. After addition of 500 mL of distilled water and 500 mL of methanol, the pH of the resultant reaction solution was adjusted to 8.5 with adding a 28percent ammonia solution (about 51 mL). An organic layer was separated, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure. 150 mL of methanol was added to the resultant concentrate, stirred for one hour, and filtered. A filtrate was washed with 100 mL of methanol to give a humid oltipraz crude crystal (12.0 to 13.0 g). The oltipraz crude crystal was placed in a reactor. 400 mL of acetonitrile was added and dissolved at 80 °C. 1.4 g of activated carbon was added and stirred for 30 minutes. The resultant solution was filtered, washed with 100 mL of acetonitrile, crystallized with stirring at a temperature of 20 to 25°C for 2 hours, and again stirred at 10°C for one hour. The obtained crystal was filtered, washed with 20 mL of acetonitrile, and vacuum dried at 40 °C to give 6.37 g of oltipraz (13.6percent yield, >99.5percent purity). NMR (6 CDC13) : 2.51 (s, 3H), 8.70 (d, 1H), 8.80 (d, 1H), 9.21 (s, 1H) |
With diphosphorus pentasulfide; | Step 3 (treatment of methyl-2-methyl-3-(pyrazin-2-yl)-3-oxopropionate with phosphorus pentasulfide to form oltipraz): |
With tetraphosphorus decasulfide; In toluene; at 95 - 97℃; for 36h; | ? Charged ST-602 in toluene (-3.5 L; 3-4 vol) to P2S5 (1931 g) in toluene (10 L; 10 vol). Rinsed with toluene (1 L; 1 vol). No exothermic effect, yellow slurry. (0184) ? Reaction over after 36 h at 95-97 °C (0185) 36 h, -95 °C, IPC HPLC lot2463-54-l: 95.2percent of ST-617 at 6.85 min and 4.8percent of ST-602 at 4.79 min (0186) ? Work-up (after 36 h at -95 °C): Cooled to RT over 20 mins (0187) ? Charged the slurry via a transfer line to a mixture of Na2C03 (2686 g; 3.5 eq), water (15 L; 15 vol) and THF (5 L; 5 vol) at 15/30 °C over a minimum of 1 h - weak exothermic effect and no gas evolution observed. (0188) ? The resulting mixture was slowly transferred back to the parent flask - some gas evolution observed. Minor insolubles were observed. (0189) ? The resulting mixture was stirred at RT for 65 h (shouldn't need more than 12 h) to complete gas evolution/quench of the reaction mixture (0190) ? The resulting mixture was passed through a 0.5" celite bed to remove fine insolubles. ? The organic layer was separated, dried with Na2S04 (200 g; 0.2 g/g SM) and concentrated under reduced pressure at (0191) ? The resulting slurry was diluted with MeOH (1.5 L; 1.5 vol) and stirred at RT for 2 h. · The solids were collected by filtration, rinsed with MeOH (2x500 mL; 2x 0.5 vol) followed by heptane (1 L + 0.5 L; 1 + 0.5 vol). (0192) ? Dried in air to yield constant weight. (0193) Isolated material: ST-603 (crude ST-617) (0194) Lot No.: 2463-55- 1 (0195) Appearance: red solid powder (crystals not uniform) (0196) Yield: 223 g (14percent) (0197) HPLC: 99percent by R&D method |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With diphosphorus pentasulfide; In toluene; | EXAMPLE 2 By proceeding as in Example 1 but starting with ethyl 2-methyl-3-(pyrazin-2-yl)-3-oxopropionate (41.2 g) and phosphorus pentasulphide (42.4 g) suspended in toluene (410 cc), 4-methyl-5-(pyrazin-2-yl)-1,2-dithiole-3-thione (3.42 g), melting at 164° C, is obtained from recrystallisation of the residue from 1,2-dichloroethane (30 cc). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With P2S5; conc. ammonia; In methanol; water; toluene; acetonitrile; | To a 3L 3-neck round-bottomed flask fitted with pressure-equalising dropping funnel with N2 inlet, condenser with N2 outlet and mechanical stirrer and under a nitrogen atmosphere was charged P2S5 (168.83 g, 759.58 mmol). Toluene (500 mL) was charged to the flask and the slurry was stirred at 20° C. Methyl-2-methyl-3-(pyrazin-2-yl)-3-oxopropionate in toluene (400 mL) (from step 2 of the process) was charged to the slurry in one portion. The resulting yellow slurry was heated to reflux temperature (110° C.) (external oil bath at;135° C.) and stirred at this temperature for 18 hours. The resulting deep red-coloured slurry was cooled to 0-5° C., water was added and the resulting suspension brought to pH 8-8.5 by the addition of conc. ammonia solution (270 mL). The resulting biphasic solution was filtered to remove solid particulates, the black lower aqueous phase was removed and the deep red-coloured upper organic phase (approx. 1L) was retained and combined with the toluene extracts (2*400 mL) of the aqueous phase. The organic phase was dried over magnesium sulphate (30 g) and concentrated in vacuo at;45° C. to a volume of 100 mL. Methanol (100 mL) was added and the resulting slurry was stirred for 20 minutes, then filtered through a sintered funnel and washed with methanol (2*20 mL). The dark red solid was dissolved in acetonitrile (approx. 400 mL) at;78° C., 1.4 g of decolorizing charcoal was added, the solution was filtered and a red precipitate was formed by cooling to 0-5° C. The precipitate was filtered and washed with ice cold acetonitrile (1*40 mL) to afford Oltipraz as bright red needles, (approx. 6.5 g, 10percent), m.p. 167-168° C., structure confirmed by 1H NMR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
53% | A mixture of 1b (100 mg, 0.4 mmol) and NaSMe (309 mg,4.4 mmol) was dissolved in MeOH (10 ml) and 0.01 M aqueoussolution of NH4OAc (10 ml). The mixture was stirred at rt for3 h. CH3I (627 mg, 4.4 mmol) was added to the reaction mixtureand stirred at rt for 3 h. After completing the reaction (TLC monitoring),MeOH was removed in vacuo. The mixture was extractedwith EtOAc twice, and the extract was washed with brine, driedover anhydrous Na2SO4 and then filtered. The filtrate was concentratedand purified by chromatography on silica gel to yield 2b asfree base form. The purified compound was added 1.25 M HClmethanol solution and stirred at rt for 1 h. The solvent wasremoved and the residue was precipitated in Et2O to afford 2b(57 mg, 53percent) as a yellow HCl salt. Mp 162 C (dec.); 1H NMR(CDCl3, 400 MHz, determined as free base) d 8.99 (s, 1H), 8.21(dd, 1H, J = 4.9, 1.5 Hz), 7.70 (d, 1H, J = 4.9 Hz), 2.50 (s, 3H), 2.30(s, 3H), 2.22 (s, 3H); 13C NMR (CDCl3, 100 MHz, determined as freebase) d 143.2, 136.0, 131.3, 128.5, 116.3, 115.9, 108.1, 20.5, 17.8,10.6; HRMS-DART (m/z): [MCl]+ calcd for C10H13ClN2S2,225.0515, found, 225.0492. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In chloroform at 20℃; for 0.166667h; | 1 Example 1: Method to make the hydrochloride of Oltipraz: (+) rotomer Example 1: Method to make the hydrochloride of Oltipraz: (+) rotomer [0064] 20 mg of synthesized oltipraz powder (ST-617-API, discussed below) is recry stallized using acetonitrile:water and added into a 5 ml glass vial equipped with a rubber septum. To the vial is added 1 ml of dry chloroform at room temperature and the vial set on a vibrating table until the solution is clear. Using a gas syringe, 5 ml of anhydrous hydrochloric acid gas is slowly bubbled into the solution over 5 minutes with intermittent shaking of the vial. Once all the HC1 gas has been added, the vial is shaken for 5 minutes, the septum is removed, and the solvent gently evaporated under a slow steady stream of nitrogen gas to give the hydrochloride complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1203/1211 (relative intensity 3:7) and 433/421 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20℃; for 0.25h; | 3 Example 3: Method to make the acetyl chloride complex of oltipraz: (+) rotomer 20 mg of synthesized oltipraz powder is recry stallized using acetone:water and added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the solution is clear. Using a syringe, 5 ml of anhydrous acetyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the acetyl chloride has been added, the vial is shaken for 15 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the acetyl chloride complex of oltipraz as an orange solid. FTIR: C=S peaks 1202/1212 (relative intensity 3:7) and 432/422 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20 - 65℃; for 0.5h; | 4 Example 4: Method to make the n-butyl chloride complex of oltipraz: (+) rotomer 20 mg of synthesized oltipraz powder is recry stallized using acetone:water and added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 5 ml of n-butyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the n-butyl chloride has been added, the vial is warmed to 65° C and shaken for 30 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the n-butyl chloride complex of oltipraz as a red solid. FTIR: C=S peaks 1201/1213 (relative intensity 2:8) and 433/421 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20 - 120℃; for 3h; | 5 Example 5: Method to make the methyl iodide complex of oltipraz: (+) rotomer 50 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a pressure-rated glass vial equipped with a screw seal. To the vial was added 20 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 10 ml of methyl iodide is slowly added into the solution with intermittent shaking of the vial. Once all the methyl iodide has been added, the vial is sealed and heated to 120° C under pressure and shaken for 3 hours (“hrs”), the vial is cooled and unsealed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the methyl iodide complex of oltipraz as a red/brown solid. FTIR: C=S peaks 1197/1214 (relative intensity 2:8) and 431/419 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20℃; for 0.25h; | 6 Example 6: Method to make the benzoyl chloride complex of oltipraz: (+) rotomer 20 mg of crude oltipraz powder is added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 1 ml of anhydrous benzoyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the benzoyl chloride has been added, the vial is shaken for 15 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under 10 mm Hg vacuum to give the benzoyl chloride complex of oltipraz as a red solid. FTIR: C=S peaks 1200/1213 (relative intensity 3:7) and 431/419 (relative intensity 3:7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone at 20℃; for 3h; Reflux; | 7 Example 7: Method to make the diethyl dithiophosphate complex of Oltipraz: (-) rotomer 22 mg of synthesized oltipraz powder is recry stallized using acetone:water and added into a glass round bottom flask equipped with a magnetic stirrer and cold-water condenser. To the flask was added 10 ml of acetone at room temperature and 20 mg of diethyl dithiophosphate ammonium salt is slowly added into the solution while stirring is continued. Once all the diethyl dithiophosphate has been added, the temperature is increased and set to reflux for 3 hrs. Released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 3 hrs the solvent is removed to yield the diethyl dithiophosphate complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1201/1220 (relative intensity 9:1) and 472/444 (relative intensity 8:2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 72h; | 9 Example 9: Method to make the dimethyl phosphate complex of Oltipraz: (-) rotomer 175 mg of trimethyl phosphate was placed with 100 mg of crude oltipraz (95% purity), in a round bottom flask equipped with a condenser and stirrer and heated at 80° C for 72 hr. After 72 hrs, the mixture is cooled to room temperature and washed with 50 ml of toluene five times. 255 g of orange/red dimethyl phosphate complex of N-methyl oltipraz is collected from the lower layer and dried under vacuum at 60° C. FTIR: C=S peaks 1210/1227 (relative intensity 9: 1) and 489/453 (relative intensity 9: 1) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone; for 6.0h;Reflux; | 22 mg of crude oltipraz powder is added into a glass round bottom flask equipped with a magnetic stirrer and cold-water condenser. To the flask was added 10 ml of acetone at room temperature and 30 mg of <strong>[57267-78-4]isethionic acid ammonium salt</strong> is slowly added into the solution while stirring is continued. Once all the <strong>[57267-78-4]isethionic acid ammonium salt</strong> has been added, the temperature is increased and set to reflux for 6 hrs. Released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 6 hrs the reaction is brought to pH 6.8 with minimum quantity of concentrated hydrochloric acid and the resultant mixture is evaporated, under vacuum, to dryness to yield the isethionic acid complex of oltipraz as a red/brown solid. FTIR: C=S peaks 1216/1228 (relative intensity 9: 1) and 464/435 (relative intensity 9: 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 20℃; for 1h; Reflux; | 11 Example 11: Method to make the thiobenzoic acid complex of Oltipraz: (-) rotomer 20 mg of crude oltipraz powder is added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 1 ml of thiobenzoic acid ammonium salt is slowly added into the solution with intermittent shaking of the vial. Once all the thiobenzoic acid ammonium salt has been added, the temperature is increased and set to reflux for 1 hr. The released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 1 hour the contents are removed under vacuum to yield the thiobenzoic acid complex of oltipraz as an orange solid. FTIR: C=S peaks 1210/1223 (relative intensity 9:1) and 474/438 (relative intensity 9:1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With hydrogenchloride In chloroform for 0.166667h; | 1 Example 1: Method to make the hydrochloride of Oltipraz: (+) rotomer 20 mg of synthesized oltipraz powder (ST-617-API, discussed below) is recrystallized using acetonitrile:water and added into a 5 ml glass vial equipped with a rubber septum. To the vial is added 1 ml of dry chloroform at room temperature and the vial set on a vibrating table until the solution is clear. Using a gas syringe, 5 ml of anhydrous hydrochloric acid gas is slowly bubbled into the solution over 5 minutes with intermittent shaking of the vial. Once all the HC1 gas has been added, the vial is shaken for 5 minutes, the septum is removed, and the solvent gently evaporated under a slow steady stream of nitrogen gas to give the hydrochloride complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1203/1211 (relative intensity 3:7) and 433/421 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
20 mg of synthesized oltipraz powder is recrystallized using acetonitrile:water and added into a 10 ml glass vial equipped with a rubber septum. All moisture is removed from the vial by nitrogen gas using a gas syringe. The vial is placed in an ice-bath and into it is added a pre chilled (10 C) solution of 22 mg of (+)-diacetyl-L-tartaric anhydride in 5 ml of ultra-dry acetone, shaken on a vibrating table for 5 minutes, and after 5 minutes is added 0.5 ml of glacial acetic acid over 30 seconds, using a syringe. After 4 h at 0 - 10 C with intermittent shaking, the vial is allowed to come to room temperature. The septum is removed, and the solvent gently evaporated under a slow steady stream of nitrogen gas to give the hydroxymaleate anhydride complex of oltipraz (see FIG. 5) as orange solid. The complex is washed 3 times with ethyl ether to remove traces of acetic acid. FTIR: C=S peaks 1201/1214 (relative intensity 8:2) and 434/423 (relative intensity 8:2). A 2 mg sample of the oltipraz-complex is ground with KBR and made into a standard pellet for FTIR analysis on a Perkin Elmer 1600 series FTIR. |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 0.25h; | 3 Example 3: Method to make the acetyl chloride complex of oltipraz: (+) rotomer 20 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the solution is clear. Using a syringe, 5 ml of anhydrous acetyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the acetyl chloride has been added, the vial is shaken for 15 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the acetyl chloride complex of oltipraz as an orange solid. FTIR: C=S peaks 1202/1212 (relative intensity 3:7) and 432/422 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 65℃; for 0.5h; | 4 Example 4: Method to make the n-butyl chloride complex of oltipraz: (+) rotomer 20 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 5 ml of n-butyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the n-butyl chloride has been added, the vial is warmed to 65° C and shaken for 30 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the n-butyl chloride complex of oltipraz as a red solid. FTIR: C=S peaks 1201/1213 (relative intensity 2:8) and 433/421 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform at 120℃; for 3h; Sealed tube; | 5 Example 5: Method to make the methyl iodide complex of oltipraz: (+) rotomer 50 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a pressure-rated glass vial equipped with a screw seal. To the vial was added 20 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 10 ml of methyl iodide is slowly added into the solution with intermittent shaking of the vial. Once all the methyl iodide has been added, the vial is sealed and heated to 120° C under pressure and shaken for 3 hours (“hrs”), the vial is cooled and unsealed, and the solvent and excess reagent gently evaporated under a slow steady stream of nitrogen gas to give the methyl iodide complex of oltipraz as a red/brown solid. FTIR: C=S peaks 1197/1214 (relative intensity 2:8) and 431/419 (relative intensity 2:8). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 0.25h; | 6 Example 6: Method to make the benzoyl chloride complex of oltipraz: (+) rotomer 20 mg of crude oltipraz powder is added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 1 ml of anhydrous benzoyl chloride is slowly added into the solution with intermittent shaking of the vial. Once all the benzoyl chloride has been added, the vial is shaken for 15 minutes, the septum is removed, and the solvent and excess reagent gently evaporated under 10 mm Hg vacuum to give the benzoyl chloride complex of oltipraz as a red solid. FTIR: C=S peaks 1200/1213 (relative intensity 3:7) and 431/419 (relative intensity 3:7). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 3h; Reflux; | 7 Example 7: Method to make the diethyl dithiophosphate complex of Oltipraz: (-) rotomer 22 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a glass round bottom flask equipped with a magnetic stirrer and cold-water condenser. To the flask was added 10 ml of acetone at room temperature and 20 mg of diethyl dithiophosphate ammonium salt is slowly added into the solution while stirring is continued. Once all the diethyl dithiophosphate has been added, the temperature is increased and set to reflux for 3 hrs. Released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 3 hrs the solvent is removed to yield the diethyl dithiophosphate complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1201/1220 (relative intensity 9: 1) and 472/444 (relative intensity 8:2) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In acetone for 3h; Reflux; | 8 Example 8: Method to make the diethyl thiophosphate complex of Oltipraz: (-) rotomer 22 mg of synthesized oltipraz powder is recrystallized using acetone:water and added into a glass round bottom flask equipped with a magnetic stirrer and cold-water condenser. To the flask was added 10 ml of acetone at room temperature and 19 mg of diethyl thiophosphate ammonium salt is slowly added into the solution while stirring is continued. Once all the diethyl thiophosphate has been added, the temperature is increased and set to reflux for 3 hrs. Released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 3 hrs the solvent is removed to yield the diethyl dithiophosphate complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1208/1221 (relative intensity 9: 1) and 479/442 (relative intensity 9: 1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In chloroform for 1h; Reflux; | 11 Example 11: Method to make the thiobenzoic acid complex of Oltipraz: (-) rotomer 20 mg of crude oltipraz powder is added into a glass vial equipped with a rubber septum. To the vial was added 10 ml of dry chloroform at room temperature and the vial set on a vibrating table until the resulting solution is clear. Using a syringe, 1 ml of thiobenzoic acid ammonium salt is slowly added into the solution with intermittent shaking of the vial. Once all the thiobenzoic acid ammonium salt has been added, the temperature is increased and set to reflux for 1 hr. The released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 1 hour the contents are removed under vacuum to yield the thiobenzoic acid complex of oltipraz as an orange solid. FTIR: C=S peaks 1210/1223 (relative intensity 9: 1) and 474/438 (relative intensity 9: 1) |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With mercury(II) diacetate; acetic acid In dichloromethane at 20℃; for 24h; | General procedure: Dithiolones were obtained by treatment of the corresponding dithiolethioneswith mercuric acetate in a dichloromethane and acetic acid mixture for 24 hours atroom temperature following a previously described method (Klingsberg, 1972). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
In water; acetone at 20℃; for 3h; Reflux; | 8 Example 8: Method to make the diethyl thiophosphate complex of Oltipraz: (-) rotomer 22 mg of synthesized oltipraz powder is recry stallized using acetone:water and added into a glass round bottom flask equipped with a magnetic stirrer and cold-water condenser. To the flask was added 10 ml of acetone at room temperature and 19 mg of diethyl thiophosphate ammonium salt is slowly added into the solution while stirring is continued. Once all the diethyl thiophosphate has been added, the temperature is increased and set to reflux for 3 hrs. Released ammonia is captured in a dilute hydrochloric acid trap from the top of the condenser. After 3 hrs the solvent is removed to yield the diethyl dithiophosphate complex of oltipraz as an orange/red solid. FTIR: C=S peaks 1208/1221 (relative intensity 9:1) and 479/442 (relative intensity 9:1). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
at 80℃; for 72h; | 9 Example 9: Method to make the dimethyl phosphate complex of Oltipraz: (-) rotomer [0072] 175 mg of trimethyl phosphate was placed with 100 mg of crude oltipraz (95% purity), in a round bottom flask equipped with a condenser and stirrer and heated at 80° C for 72 hr. After 72 hrs, the mixture is cooled to room temperature and washed with 50 ml of toluene five times. 255 g of orange/red dimethyl phosphate complex ofN-methyl oltipraz is collected from the lower layer and dried under vacuum at 60° C. FTIR: C=S peaks 1210/1227 (relative intensity 9:1) and 489/453 (relative intensity 9:1) . |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
With acetic acid; In acetone; at 0 - 10℃; for 4.58333h; | 20 mg of synthesized oltipraz powder is recrystallized using acetonitrile:water and added into a 10 ml glass vial equipped with a rubber septum. All moisture is removed from the vial by nitrogen gas using a gas syringe. The vial is placed in an ice-bath and into it is added a pre-chilled (10 C) solution of 22 mg of (+)-diacetyl-L-tartaric anhydride in 5 ml of ultra-dry acetone, shaken on a vibrating table for 5 minutes, and after 5 minutes is added 0.5 ml of glacial acetic acid over 30 seconds, using a syringe. After 4 h at 0 - 10 C with intermittent shaking, the vial is allowed to come to room temperature. The septum is removed, and the solvent gently evaporated under a slow steady stream of nitrogen gas to give the hydroxymaleate anhydride complex of oltipraz (see FIG. 5) as orange solid. The complex is washed 3 times with ethyl ether to remove traces of acetic acid. FTIR: C=S peaks 1201/1214 (relative intensity 8:2) and 434/423 (relative intensity 8:2). A 2 mg sample of the oltipraz-complex is ground with KBR and made into a standard pellet for FTIR analysis on a Perkin Elmer 1600 series FTIR. |
Tags: 64224-21-1 synthesis path| 64224-21-1 SDS| 64224-21-1 COA| 64224-21-1 purity| 64224-21-1 application| 64224-21-1 NMR| 64224-21-1 COA| 64224-21-1 structure
Precautionary Statements-General | |
Code | Phrase |
P101 | If medical advice is needed,have product container or label at hand. |
P102 | Keep out of reach of children. |
P103 | Read label before use |
Prevention | |
Code | Phrase |
P201 | Obtain special instructions before use. |
P202 | Do not handle until all safety precautions have been read and understood. |
P210 | Keep away from heat/sparks/open flames/hot surfaces. - No smoking. |
P211 | Do not spray on an open flame or other ignition source. |
P220 | Keep/Store away from clothing/combustible materials. |
P221 | Take any precaution to avoid mixing with combustibles |
P222 | Do not allow contact with air. |
P223 | Keep away from any possible contact with water, because of violent reaction and possible flash fire. |
P230 | Keep wetted |
P231 | Handle under inert gas. |
P232 | Protect from moisture. |
P233 | Keep container tightly closed. |
P234 | Keep only in original container. |
P235 | Keep cool |
P240 | Ground/bond container and receiving equipment. |
P241 | Use explosion-proof electrical/ventilating/lighting/equipment. |
P242 | Use only non-sparking tools. |
P243 | Take precautionary measures against static discharge. |
P244 | Keep reduction valves free from grease and oil. |
P250 | Do not subject to grinding/shock/friction. |
P251 | Pressurized container: Do not pierce or burn, even after use. |
P260 | Do not breathe dust/fume/gas/mist/vapours/spray. |
P261 | Avoid breathing dust/fume/gas/mist/vapours/spray. |
P262 | Do not get in eyes, on skin, or on clothing. |
P263 | Avoid contact during pregnancy/while nursing. |
P264 | Wash hands thoroughly after handling. |
P265 | Wash skin thouroughly after handling. |
P270 | Do not eat, drink or smoke when using this product. |
P271 | Use only outdoors or in a well-ventilated area. |
P272 | Contaminated work clothing should not be allowed out of the workplace. |
P273 | Avoid release to the environment. |
P280 | Wear protective gloves/protective clothing/eye protection/face protection. |
P281 | Use personal protective equipment as required. |
P282 | Wear cold insulating gloves/face shield/eye protection. |
P283 | Wear fire/flame resistant/retardant clothing. |
P284 | Wear respiratory protection. |
P285 | In case of inadequate ventilation wear respiratory protection. |
P231 + P232 | Handle under inert gas. Protect from moisture. |
P235 + P410 | Keep cool. Protect from sunlight. |
Response | |
Code | Phrase |
P301 | IF SWALLOWED: |
P304 | IF INHALED: |
P305 | IF IN EYES: |
P306 | IF ON CLOTHING: |
P307 | IF exposed: |
P308 | IF exposed or concerned: |
P309 | IF exposed or if you feel unwell: |
P310 | Immediately call a POISON CENTER or doctor/physician. |
P311 | Call a POISON CENTER or doctor/physician. |
P312 | Call a POISON CENTER or doctor/physician if you feel unwell. |
P313 | Get medical advice/attention. |
P314 | Get medical advice/attention if you feel unwell. |
P315 | Get immediate medical advice/attention. |
P320 | |
P302 + P352 | IF ON SKIN: wash with plenty of soap and water. |
P321 | |
P322 | |
P330 | Rinse mouth. |
P331 | Do NOT induce vomiting. |
P332 | IF SKIN irritation occurs: |
P333 | If skin irritation or rash occurs: |
P334 | Immerse in cool water/wrap n wet bandages. |
P335 | Brush off loose particles from skin. |
P336 | Thaw frosted parts with lukewarm water. Do not rub affected area. |
P337 | If eye irritation persists: |
P338 | Remove contact lenses, if present and easy to do. Continue rinsing. |
P340 | Remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P341 | If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P342 | If experiencing respiratory symptoms: |
P350 | Gently wash with plenty of soap and water. |
P351 | Rinse cautiously with water for several minutes. |
P352 | Wash with plenty of soap and water. |
P353 | Rinse skin with water/shower. |
P360 | Rinse immediately contaminated clothing and skin with plenty of water before removing clothes. |
P361 | Remove/Take off immediately all contaminated clothing. |
P362 | Take off contaminated clothing and wash before reuse. |
P363 | Wash contaminated clothing before reuse. |
P370 | In case of fire: |
P371 | In case of major fire and large quantities: |
P372 | Explosion risk in case of fire. |
P373 | DO NOT fight fire when fire reaches explosives. |
P374 | Fight fire with normal precautions from a reasonable distance. |
P376 | Stop leak if safe to do so. Oxidising gases (section 2.4) 1 |
P377 | Leaking gas fire: Do not extinguish, unless leak can be stopped safely. |
P378 | |
P380 | Evacuate area. |
P381 | Eliminate all ignition sources if safe to do so. |
P390 | Absorb spillage to prevent material damage. |
P391 | Collect spillage. Hazardous to the aquatic environment |
P301 + P310 | IF SWALLOWED: Immediately call a POISON CENTER or doctor/physician. |
P301 + P312 | IF SWALLOWED: call a POISON CENTER or doctor/physician IF you feel unwell. |
P301 + P330 + P331 | IF SWALLOWED: Rinse mouth. Do NOT induce vomiting. |
P302 + P334 | IF ON SKIN: Immerse in cool water/wrap in wet bandages. |
P302 + P350 | IF ON SKIN: Gently wash with plenty of soap and water. |
P303 + P361 + P353 | IF ON SKIN (or hair): Remove/Take off Immediately all contaminated clothing. Rinse SKIN with water/shower. |
P304 + P312 | IF INHALED: Call a POISON CENTER or doctor/physician if you feel unwell. |
P304 + P340 | IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing. |
P304 + P341 | IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing. |
P305 + P351 + P338 | IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing. |
P306 + P360 | IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes. |
P307 + P311 | IF exposed: call a POISON CENTER or doctor/physician. |
P308 + P313 | IF exposed or concerned: Get medical advice/attention. |
P309 + P311 | IF exposed or if you feel unwell: call a POISON CENTER or doctor/physician. |
P332 + P313 | IF SKIN irritation occurs: Get medical advice/attention. |
P333 + P313 | IF SKIN irritation or rash occurs: Get medical advice/attention. |
P335 + P334 | Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages. |
P337 + P313 | IF eye irritation persists: Get medical advice/attention. |
P342 + P311 | IF experiencing respiratory symptoms: call a POISON CENTER or doctor/physician. |
P370 + P376 | In case of fire: Stop leak if safe to Do so. |
P370 + P378 | In case of fire: |
P370 + P380 | In case of fire: Evacuate area. |
P370 + P380 + P375 | In case of fire: Evacuate area. Fight fire remotely due to the risk of explosion. |
P371 + P380 + P375 | In case of major fire and large quantities: Evacuate area. Fight fire remotely due to the risk of explosion. |
Storage | |
Code | Phrase |
P401 | |
P402 | Store in a dry place. |
P403 | Store in a well-ventilated place. |
P404 | Store in a closed container. |
P405 | Store locked up. |
P406 | Store in corrosive resistant/ container with a resistant inner liner. |
P407 | Maintain air gap between stacks/pallets. |
P410 | Protect from sunlight. |
P411 | |
P412 | Do not expose to temperatures exceeding 50 oC/ 122 oF. |
P413 | |
P420 | Store away from other materials. |
P422 | |
P402 + P404 | Store in a dry place. Store in a closed container. |
P403 + P233 | Store in a well-ventilated place. Keep container tightly closed. |
P403 + P235 | Store in a well-ventilated place. Keep cool. |
P410 + P403 | Protect from sunlight. Store in a well-ventilated place. |
P410 + P412 | Protect from sunlight. Do not expose to temperatures exceeding 50 oC/122oF. |
P411 + P235 | Keep cool. |
Disposal | |
Code | Phrase |
P501 | Dispose of contents/container to ... |
P502 | Refer to manufacturer/supplier for information on recovery/recycling |
Physical hazards | |
Code | Phrase |
H200 | Unstable explosive |
H201 | Explosive; mass explosion hazard |
H202 | Explosive; severe projection hazard |
H203 | Explosive; fire, blast or projection hazard |
H204 | Fire or projection hazard |
H205 | May mass explode in fire |
H220 | Extremely flammable gas |
H221 | Flammable gas |
H222 | Extremely flammable aerosol |
H223 | Flammable aerosol |
H224 | Extremely flammable liquid and vapour |
H225 | Highly flammable liquid and vapour |
H226 | Flammable liquid and vapour |
H227 | Combustible liquid |
H228 | Flammable solid |
H229 | Pressurized container: may burst if heated |
H230 | May react explosively even in the absence of air |
H231 | May react explosively even in the absence of air at elevated pressure and/or temperature |
H240 | Heating may cause an explosion |
H241 | Heating may cause a fire or explosion |
H242 | Heating may cause a fire |
H250 | Catches fire spontaneously if exposed to air |
H251 | Self-heating; may catch fire |
H252 | Self-heating in large quantities; may catch fire |
H260 | In contact with water releases flammable gases which may ignite spontaneously |
H261 | In contact with water releases flammable gas |
H270 | May cause or intensify fire; oxidizer |
H271 | May cause fire or explosion; strong oxidizer |
H272 | May intensify fire; oxidizer |
H280 | Contains gas under pressure; may explode if heated |
H281 | Contains refrigerated gas; may cause cryogenic burns or injury |
H290 | May be corrosive to metals |
Health hazards | |
Code | Phrase |
H300 | Fatal if swallowed |
H301 | Toxic if swallowed |
H302 | Harmful if swallowed |
H303 | May be harmful if swallowed |
H304 | May be fatal if swallowed and enters airways |
H305 | May be harmful if swallowed and enters airways |
H310 | Fatal in contact with skin |
H311 | Toxic in contact with skin |
H312 | Harmful in contact with skin |
H313 | May be harmful in contact with skin |
H314 | Causes severe skin burns and eye damage |
H315 | Causes skin irritation |
H316 | Causes mild skin irritation |
H317 | May cause an allergic skin reaction |
H318 | Causes serious eye damage |
H319 | Causes serious eye irritation |
H320 | Causes eye irritation |
H330 | Fatal if inhaled |
H331 | Toxic if inhaled |
H332 | Harmful if inhaled |
H333 | May be harmful if inhaled |
H334 | May cause allergy or asthma symptoms or breathing difficulties if inhaled |
H335 | May cause respiratory irritation |
H336 | May cause drowsiness or dizziness |
H340 | May cause genetic defects |
H341 | Suspected of causing genetic defects |
H350 | May cause cancer |
H351 | Suspected of causing cancer |
H360 | May damage fertility or the unborn child |
H361 | Suspected of damaging fertility or the unborn child |
H361d | Suspected of damaging the unborn child |
H362 | May cause harm to breast-fed children |
H370 | Causes damage to organs |
H371 | May cause damage to organs |
H372 | Causes damage to organs through prolonged or repeated exposure |
H373 | May cause damage to organs through prolonged or repeated exposure |
Environmental hazards | |
Code | Phrase |
H400 | Very toxic to aquatic life |
H401 | Toxic to aquatic life |
H402 | Harmful to aquatic life |
H410 | Very toxic to aquatic life with long-lasting effects |
H411 | Toxic to aquatic life with long-lasting effects |
H412 | Harmful to aquatic life with long-lasting effects |
H413 | May cause long-lasting harmful effects to aquatic life |
H420 | Harms public health and the environment by destroying ozone in the upper atmosphere |
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