Structure of 1393813-42-7
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CAS No. : | 1393813-42-7 |
Formula : | C13H14BrClN4O2S |
M.W : | 405.70 |
SMILES Code : | O=S(NCCC)(NC1=NC=NC(Cl)=C1C2=CC=C(Br)C=C2)=O |
MDL No. : | MFCD25372049 |
Boiling Point : | No data available |
InChI Key : | MUPKRWAGQKVNPA-UHFFFAOYSA-N |
Pubchem ID : | 71500858 |
GHS Pictogram: |
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Signal Word: | Warning |
Hazard Statements: | H302-H315-H319-H335 |
Precautionary Statements: | P261-P264-P270-P271-P280-P301+P312-P302+P352-P304+P340-P305+P351+P338-P330-P332+P313-P337+P313-P362-P403+P233-P405-P501 |
* 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 |
---|---|---|
110 g | With sodium amide; In dimethyl sulfoxide; at 25 - 30℃; for 10h;Inert atmosphere; | To a solution of 5-(4-bromophenyl)-4,6-dichloro-pyrimidine (100 g) in dimethyl sulfoxide (700 ml), potassium(N-propylsulfamoyl)amide (145 g) was added at 25-30C under nitrogen atmosphere and stirred for 10 hrs. After reaction completion, pH of the reaction mass was adjusted to 2-3 using aqueous hydrochloric acid at 25-30C and stirred for 75 mins. The solid obtained was filtered, washed with water and suck dried under vacuum. Methanol (3500 ml) was added to the above compound and heated to reflux temperature then stirred for an hour at reflux. The reaction mass was distilled upto 450-550 mL remained in the flask. The reaction mass was cooled to 25-30C, stirred for 75 mins then further cooled to 0- 5C and stirred for 75 mins. The obtained solid was filtered, washed with methanol and dried under vacuum at 50-55C for 4 hrs to get the title compound. Yield: 110 g; Purity by HPLC: 99.10% |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
89% | A.ii. N-(5-(4-bromophenyl)-6-chloropyrimidin-4-yl)propane-1-sulfamide:tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 mi <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portionwise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HC1. The suspension was cooled to 0C and stirred for 30 mm. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to S -(4-bromophenyl)-4,6-dichloropyrimidine). | |
89% | A.ii. N- (5 -(4-bromopheny I) -6-chloropyrimidin-4-yl)propane- 1-sulfamide; tBuOK (16.0 g; 0.14 mol; 1 eq.) was added to the above prepared cold (5C) solution of Intermediate A.i in DMSO. The resulting suspension was heated to 20C and stirred for 30 min. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (10.7 g; 0.035 mol; 0.25 eq.) was added portion wise and the mixture was heated to 50C for 1 h. Water was added. The pH of the solution was adjusted to 4-5 using 33% aq. HCl. The suspension was cooled to 0C and stirred for 30 min. It was filtered off, rinsed with a solution of water and MeOH and dried under reduced pressure to yield the title compound as a white solid (12.6 g, 89% yield with respect to <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong>). | |
With lithium amide; In dimethyl sulfoxide; at 15 - 25℃; for 2h;Inert atmosphere; | To a solution of V-propylsulfamide (25.0 gm, 0.180 mol) in dimethylsulfoxide (250.0 ml) was added Lithium amide (7.6 gm, 0.33 mol) under nitrogen atmosphere at 15-25 C, followed by addition of 5-(4-bromophenyl)-4,6- dichloropyrimidine (50.0 gm, 0.164 mol). The reaction mass was stirred for 2 hr. at room temperature and the progress of reaction was monitored by HPLC. After reaction completion this reaction mass was drop wise added to the solution containing Lithium amide (7.6 gm, 0.33 mol) and ethylene glycol (250.0 ml) at 15-25 C under nitrogen atmosphere. After the addition reaction mixture was heated to 105 - 110C, maintained for 18-24 hours and the reaction progress was monitored by HPLC. After completion of reaction, resulting mass was cooled to 25-30 C and 5% w/v citric acid solution (1000.0 ml) was added to the reaction mass. The product was extracted twice with ethyl acetate (1000.0 ml x 2), further organic layer was washed twice with 10% w/v brine solution (500.0 ml x 2). Organic layer was concentrated at 55-60C under reduced pressure to produce A/-5-(4- bromophenyl)-6-(-2-hydroxyethoxy)-4-pyrimidinyl-//-propylsulfamide as a residue. The obtained residue was dissolved in methanol 65-70 C and maintained for 30 min. The resulting solution was gradually cooled to room temperature then cooled to 0-5C and maintained reaction mass at 0-5C for 60-90 min. Obtained solid was filtered, washed with methanol (50.0 ml), suck dried and dried at 55-60C to afford white solid of N-5-(4-bromophenyl)-6-(- 2hydroxyethoxy)-4-pyrimidinyl- N'-propylsulfamide. [Yield = 50.0 gm (70.48 %); Purity (HPLC) = 98.50 %]. (M + H)7z= 433.0. 1H NMR (CDCl3): delta 8.46-8.45 (s, 1 H), 7.65-7.62 (m, 2H), 7.25-7.17 (m, 2H), 6.91 (s, br, 1 H), 5.62-5.69 (t, 1 H), 4.48-4.46 (m, 2H), 3.84- 3.81 (m, 2H), 2.97-2.92 (q, 2H), 2.97-2.92 (t, 1 H), 1.16-1.52 (h, 2H), 0.94- 0.91 (t, 3H). 3C NMR (CDC ): delta 11.31 , 22.07, 44.74, 59.20, 68.32, 104.94, 121.42, 129.84, 131.55, 132.79, 155.91 , 156.38, 166.26. |
Potassium tert-butoxide(90 gm, 0.802 mol) was added in to a reaction flask containing a solution of N-Propyl-sulfamide (N-Propyl-sulfamide (82 gm, 0.593 mol) in DMSO (250 ml)) and stirred the reaction mass at room temperature for 30 min to obtain potassium salt of N- propyl sulfamide. <strong>[146533-41-7]5-(4-bromophenyl)-4,6-dichloropyrimidine</strong> (100 gm, 0.329 mol) was added in to the reaction mass and stirred the contents for 5-6 hrs at 25-30C. DM water (500 ml) was added to the reaction mass a stirred solution. Further 10% citric acid solution (500 ml) was added slowly for an about 1 -2 hrs to obtain solid. The precipitated solid was filtered and washed with DM water (120 ml) and suck dried the material for 30 min. The product was dried under vacuum at 50-55 C for 10-12 hrs to obtain title product. Yield: 137 gm; Purity (By HPLC): 92.0% | ||
With lithium amide; In dimethyl sulfoxide; at 20 - 25℃; for 2h; | To a stirred solution of 2.0 kg 5-(4-Bromophenyl)-4,6-dichloropyrimidine (2, 6.57 mol) in 20 dm3 DMSO,0.303 kg lithium amide (13.15 mol) and 1.0 kg N-propylsulfamide(3, 7.23 mol) were added at 20-25 C. The reaction mass was stirred at 20-25 C for 2-6 h (completionof the reaction was monitored by HPLC). |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
115 g | With sodium hydroxide; In dimethyl sulfoxide; at 40℃; for 6h; | 600 ml of DMSO was added to 6.4 g of Sodium hydroxide, 100 g of reacting 5-(4- bromophenyl)-4,6dichloropyrimidine, followed by 116 g of N-propyl sulfomyl amide potassium salt (Sodium salt can also be used). The reaction mixture was stirred at 40±5 C for 6 hrs. On completion of the reaction, the reaction mass was cooled to 27±2 C and 1000 ml of purified water was added. The pH was adjusted with IN HC1 solution, followed by filtration. Wet cake was further treated with purified water and heated at 50±2 C for 30 minutes, cooled at 27±2 C. The solid was filtered, washed with purified water. The water slurry wet material was further subjected to methanol purification, heated at 50±2 C for 30 mins, cooled at 27±2 C. The final solid obtained was washed with methanol and dried under vacuum at 43±2 C for 12 hours.Dry weight: 115g |
Yield | Reaction Conditions | Operation in experiment |
---|---|---|
85% | A mixture of 1 (100 g, 0.33 mol), K2CO3 (221 g, 1.6 mol), and acetonitrile (1.3 L) washeated to 50C and stirred for 20 min. The solution of 2 (43 g, 0.31 mol) in acetonitrile(200 mL) was added dropwise and maintained at 50C for 10 h. The reaction solvent wasreplaced with toluene (2 L) using a Dean-Stark apparatus. The precipitated solid was filteredand suspended in water (2 L). The pH was adjusted to 7 by using 6 N hydrochloricacid and stirred for 20 min. The resulting precipitate was filtered and dried in the oven at55C for 5 h. The crude product was recrystallized from ethyl acetate to acquire 106 g(85%) of 3 as a white solid, mp 236C-238C. IR (KBr): 3272, 2966, 1593, 1566, 1438.1H NMR (500 MHz, DMSO-d6): d 0.73-0.76 (t, JD6.9, Me); 1.30-1.36 (m, CH2), 2.52-2.56 (m, CH2), 5.68-5.71 (t, JD6.6, NH), 7.12-7.14 (d, 2 H, ArH), 7.50-7.51 (d, 2 H,ArH), 8.04 (s, 1 H, ArH). 13C NMR (125 MHz, DMSO): d 12.41, 21.63, 45.75, 120.26,120.93, 131.50, 133.38, 136.21, 155.26, 156.73, 164.76. |
Tags: 1393813-42-7 synthesis path| 1393813-42-7 SDS| 1393813-42-7 COA| 1393813-42-7 purity| 1393813-42-7 application| 1393813-42-7 NMR| 1393813-42-7 COA| 1393813-42-7 structure
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