20054-45-9|2-Mercapto-N-methylbenzamide| Ambeed

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Product Details of [ 20054-45-9 ]

CAS No. :	20054-45-9
Formula :	C₈H₉NOS
M.W :	167.23
SMILES Code :	O=C(NC)C1=CC=CC=C1S
MDL No. :	MFCD00136334
InChI Key :	VIFOAZNEQRHREM-UHFFFAOYSA-N
Pubchem ID :	4525601

Safety of [ 20054-45-9 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H317-H318
Precautionary Statements:	P261-P272-P280-P302+P352-P305+P351+P338-P501
Class:	8
UN#:	1759
Packing Group:	Ⅲ

Application In Synthesis of [ 20054-45-9 ]

* 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.

Downstream synthetic route of [ 20054-45-9 ]

[ 20054-45-9 ] Synthesis Path-Downstream 1~3

1
[ 261953-36-0 ]
[ 20054-45-9 ]
[ 944835-85-2 ]

Yield	Reaction Conditions	Operation in experiment
96%	With tris-(dibenzylideneacetone)dipalladium(0); cesiumhydroxide monohydrate; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 100℃; for 4.5h;Inert atmosphere;	N,N-Dimethylformamide (25 mL) was added to 6-iodo-1H-indazole (5.51 g, 22 mmol), 2-mercapto-N-methylbenzamide(5.16 g, 31 mmol), Pd2(dba)3 (1.02 g, 1.1 mmol), 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene (1.46 g,2.5 mmol) and cesium hydroxide monohydrate (5.67 g, 33 mmol) and stirred under an argon atmosphere at 100C for4.5 hours. The solvent was distilled away from the reaction solution under a reduced pressure, the residue was dissolvedin ethyl acetate and washed with water and saturated saline. The organic layer was dried with anhydrous sodium sulfate,and the solvent was distilled away under a reduced pressure. The residue was purified by silica gel column chromatography(hexane/ethyl acetate (v/v) = 1/3) to obtain the title compound (6.14 g, 96%) as a pale orange solid.1H NMR (400 MHz, DMSO-d6) δ 13.13 (1H, br s), 8.36 (1H, br q, J = 4.4 Hz), 8.10 (1H, s), 7.78 (1H, br d, J = 8.4 Hz),7.59 (1H, br s), 7.48-7.46 (1H, m), 7.29 (1H, td, J = 7.6, 1.6 Hz), 7.25 (1H, td, J = 7.6, 1.6 Hz), 7.08 (1H, dd, J = 8.4, 1.6Hz), 6.99-6.97 (1H, m), 2.76 (3H, d, J = 4.4 Hz)
	With cesium hydroxide; 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In 1-methyl-pyrrolidin-2-one; water; at 80℃; for 18.5h;Inert atmosphere;	A 5 L three neck flask was equipped with a mechanical stirrer, a temperature probe, and a N2 inlet. The flask was charged with 6 -iodoindazole (200 g) followed by 2 - mercapto-N-methylbenzamide (144 g), Pd2(dba)3(3.75 g), Xantphos (4.74 g), NMP (1.2 L), and 50% aqueous CsOH solution (150 mL) in that order. Stirring was then commenced. The dark reaction mixture was degassed three times by alternately connecting to house vacuum and nitrogen. The mixture was heated to 80 C over a period of half an hour and maintained at the same temperature for 18 hours. The reaction was monitored by HPLC . It was noted that heating may be discontinued when the amount of 6-diiodoindazole is < 3%. The reaction mixture was allowed to cool to room temperature. An aqueous solution of Na HSO3 was prepared by adding 90 g of solid NaHSO3 into 1.5 L of deionized water with strong stirring. This solution was then set aside until the reaction quench step as described below. The reaction mixture in the 5 L flask was chilled in an ice-water bath until an internal temperature of 0.9 C was reached. KOH (183 g) was then charged in a single portion and the resulting mixture was allowed to stir for half an hour in ice-water bath (slight exotherm, highest point 4.0 C). Iodine (417 g) was dissolved in NMP (420 mL) in a separate flask with stirring. Once complete dissolution of iodine was been confirmed, the dark mixture was charged to a 1 L addition funnel. The iodine/NMP solution was then added dropwise over 1 h to the reaction mixture. (Note: the addition is exothermic and the internal reaction temperature must therefore be controlled via external cooling in addition to the controlled addition rate; the internal tempe rature should be kept between 0 C and 16.8C). Upon complete addition the final temperature was 14.5C. The flask was then taken out of the bath and the in ternal temperature reached 21.1C in 70 min. The mixture was allowed to stir at room temperature for three hours, at which time, analysis of an aliquot sample indicated the reacti on was complete (<3% left). Upon confirmation of reaction completion (HPLC), the flask was re -immersed in the icewater bath. The aqueous NaHSO3 solution prepared as described previously was added slowly over 40 minutes from an addition funnel. ( Note: this addition is exothermic and the internal reaction temperature must therefore be controlled via external cooling in addition to the controlled addition rate; the internal temper ature should be kept below15.7 C). Upon complete addition the reaction was a slurry of light yellow solids. The mixture was allowed to stir at ambient temperature overnight. The solid produ ct was collected by filtration. The wet cake was recharged back into the 5 L flask and the funnel was rinsed with 1.5 L of water, and the r inses were also charged into the 5 L flask. The mixture was stirred for one hour and filtered. The wet cake was recharged back to the 5 L flask, and the funnel was rinsed with 1.5 L of methanol, and the rinses were also charged into the 5 L flask. The mixture was heated at 45 C for two hours, then allowed to cool. The mixture was filtered and the cake was washed with 500 mL of MeOH, and sucked dry. The product (cake) was placed in a vacuum oven at 60 C for 18 h to afford 317 g of 2-(3-lodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide.
	With cesium hydroxide;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphosphino)-9,9-dimethylxanthene; In 1-methyl-pyrrolidin-2-one; water; at 80℃; for 18.5h;	A 5 L three neck flask was equipped with a mechanical stirrer, a temperature probe, and a N2 inlet. The flask was charged with <strong>[261953-36-0]6-iodoindazole</strong> (200 g) followed by 2-mercapto-N-methylbenzamide (144 g), Pd2(dba)3 (3.75 g), Xantphos (4.74 g), NMP (1.2 L), and 50% aqueous CsOH solution (150 mL) in that order. Stirring was then commenced. The dark reaction mixture was degassed three times by alternately connecting to house vacuum and nitrogen. The mixture was heated to 80 C. over a period of half an hour and maintained at the same temperature for 18 hours. The reaction was monitored by HPLC. It was noted that heating may be discontinued when the amount of 6-diiodoindazole is <3%. The reaction mixture was allowed to cool to room temperature. An aqueous solution of NaHSO3 was prepared by adding 90 g of solid NaHSO3 into 1.5 L of deionized water with strong stirring. This solution was then set aside until the reaction quench step as described below. The reaction mixture in the 5 L flask was chilled in an ice-water bath until an internal temperature of 0.9 C. was reached. KOH (183 g) was then charged in a single portion and the resulting mixture was allowed to stir for half an hour in ice-water bath (slight exotherm, highest point 4.0 C.). Iodine (417 g) was dissolved in NMP (420 mL) in a separate flask with stirring. Once complete dissolution of iodine was been confirmed, the dark mixture was charged to a 1 L addition funnel. The iodine/NMP solution was then added dropwise over 1 h to the reaction mixture. (Note: the addition is exothermic and the internal reaction temperature must therefore be controlled via external cooling in addition to the controlled addition rate; the internal temperature should be kept between 0 C. and 16.8 C.). Upon complete addition the final temperature was 14.5 C. The flask was then taken out of the bath and the internal temperature reached 21.1 C. in 70 min. The mixture was allowed to stir at room temperature for three hours, at which time, analysis of an aliquot sample indicated the reaction was complete (<3% left). Upon confirmation of reaction completion (HPLC), the flask was re-immersed in the ice-water bath. The aqueous NaHSO3 solution prepared as described previously was added slowly over 40 minutes from an addition funnel. (Note: this addition is exothermic and the internal reaction temperature must therefore be controlled via external cooling in addition to the controlled addition rate; the internal temperature should be kept below 15.7 C.). Upon complete addition the reaction was a slurry of light yellow solids. The mixture was allowed to stir at ambient temperature overnight. The solid product was collected by filtration. The wet cake was recharged back into the 5 L flask and the funnel was rinsed with 1.5 L of water, and the rinses were also charged into the 5 L flask. The mixture was stirred for one hour and filtered. The wet cake was recharged back to the 5 L flask, and the funnel was rinsed with 1.5 L of methanol, and the rinses were also charged into the 5 L flask. The mixture was heated at 45 C. for two hours, then allowed to cool. The mixture was filtered and the cake was washed with 500 mL of MeOH, and sucked dry. The product (cake) was placed in a vacuum oven at 60 C. for 18 h to afford 317 g of 2-(3-Iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide.

References: [1]Patent: EP3127900,2017,A1 .Location in patent: Paragraph 0252; 0253.
[2]Patent: EP2163544,2010,A1 .Location in patent: Page/Page column 36-37.
[3]Patent: US2006/94881,2006,A1 .Location in patent: Page/Page column 26; 27.
[4]Organic Process Research and Development,2014,vol. 18,p. 266 - 274.
[5]Green Chemistry,2015,vol. 17,p. 225 - 230.

2
[ 319472-78-1 ]
[ 20054-45-9 ]
[ 885126-34-1 ]

Yield	Reaction Conditions	Operation in experiment
	With cesium hydroxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 70℃; for 0.5h;	<strong>[319472-78-1]3,6-diiodoindazole</strong> (250.00 g), 2-mercapto-N-methylbenzamide (118.48 g), Pd2(dba)3 (9.28 g), Xantphos (11.73 g), DMF (2.5 L, 10 mL/g), followed by CsOH were added sequentially to a 5 L four-neck flask equipped with a mechanical stirrer and a temperature probe. The reaction mixture was then stirred. The dark mixture was degassed three times by alternately connecting to house vacuum and then nitrogen. The mixture was heated to 70 C over a period of 30 minutes and maintained at the same temperature for fours, at which time HPLC of the EPO <DP n="30"/>aliquot indicated that the <strong>[319472-78-1]3,6-diiodoindazole</strong> was less than 3%. After cooling, the mixture was poured into a mixture of 7.5 L of water, 1.25 L of toluene and 1.25 L of CH2CI2 in a 22 L extractor. The mixture was allowed to stir at ambient temperature overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was further dried at 35 C under house vacuum for six hours to afford 216 g of the final product. The mother liquor was then extracted with 1.5 L of EtOAc. After partitioning, the aqueous layer was discarded. The organic layer was washed twice each with 2 L of water and concentrated. The residue was treated with 250 mL of CH2CI2 and stored overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was dried at 35 0C under house vacuum overnight to afford 24.71 g of the final product. The combined yield was 241 g of the final product. The material showed satisfactory purity and was used in the next step without further purification. 1H NMR 300MHz, DMSO ppm: 13.53 (s, 1 H), 8.35 (q, J=4.7 Hz, 1 H), 7.56 (s, 1H), 7.51-7.40 (m, 2H), 7.36-7.23 (m, 3H), 7.13 (dd, J=8.5, 1.3 Hz, 1H), 7.06-7.01 (m, 1 H), 2.76 (d, J=4.7 Hz, 3H).
	With cesium hydroxide; 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene;tris-(dibenzylideneacetone)dipalladium(0); In N,N-dimethyl-formamide; at 20 - 70℃;Inert atmosphere;	<strong>[319472-78-1]3,6-diiodoindazole</strong> (250.00 g), 2 -mercapto-N-methylbenzamid e (118.48 g), Pd 2(dba)3 (9.28 g), Xantphos (11.73 g), DMF (2.5 L, 10 mL/g), followed by CSOH were added sequentially to a 5 L four-neck flask equipped with a mechanical stirrer and a temperature probe. The reaction mixture was then stirred. The dark mixt ure was degassed three times by alternately connecting to house vacuum and then nitrogen. The mixture was heated to 70 C over a period of 30 minutes and maintained at the same temperature for fours, at which time HPLC of the aliquot indicated that the 3, 6-diiodoindazole was less than 3%. After cooling, the mixture was poured into a mixture of 7.5 L of water, 1.25 L of toluene and 1.25 L of CH2Cl2 in a 22 L extractor. The mixture was allowed to stir at ambient temperature overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was further dried at 35 C under house vacuum for six hours to afford 216 g of the final productproduct. The mother liquor was then extracted with 1.5 L of EtOAc. After partition ing, the aqueous layer was discarded. The organic layer was washed twice each with 2 L of water and concentrated. The residue was treated with 250 mL of CH 2Cl2 and stored overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was dried at 35 C under house vacuum overnight to afford 24.71 g of the final productproduct. The combined yield was 241 g of the final productproduct. The material showed satisfactory purity and was used in the next step without furth er purification. 1H NMR 300MHz, DMSO ppm: 13.53 (s, 1H), 8.35 (q, J=4.7 Hz, 1H), 7.56 (s, 1H), 7.51 - 7.40 (m, 2H), 7.36-7.23 (m, 3H), 7.13 (dd, J=8.5, 1.3 Hz, 1 H), 7.06 -7.01 (m, 1 H), 2.76 (d, J=4.7 Hz, 3H).
	With cesium hydroxide;tris-(dibenzylideneacetone)dipalladium(0); 4,5-bis(diphenylphos4,5-bis(diphenylphosphino)-9,9-dimethylxanthenephino)-9,9-dimethylxanthene; In N,N-dimethyl-formamide; at 70℃; for 4.5h;Product distribution / selectivity;	Example 2 Preparation of 2-(3-Iodo-1H-indazol-6-ylsulfanyl)-N-methyl-benzamide <strong>[319472-78-1]3,6-diiodoindazole</strong> (250.00 g), 2-mercapto-N-methylbenzamide (118.48 g), Pd2(dba)3 (9.28 g), Xantphos (11.73 g), DMF (2.5 L, 10 mL/g), followed by CsOH were added sequentially to a 5 L four-neck flask equipped with a mechanical stirrer and a temperature probe. The reaction mixture was then stirred. The dark mixture was degassed three times by alternately connecting to house vacuum and then nitrogen. The mixture was heated to 70 C. over a period of 30 minutes and maintained at the same temperature for fours, at which time HPLC of the aliquot indicated that the <strong>[319472-78-1]3,6-diiodoindazole</strong> was less than 3%. After cooling, the mixture was poured into a mixture of 7.5 L of water, 1.25 L of toluene and 1.25 L of CH2Cl2 in a 22 L extractor. The mixture was allowed to stir at ambient temperature overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was further dried at 35 C. under house vacuum for six hours to afford 216 g of the final productproduct. The mother liquor was then extracted with 1.5 L of EtOAc. After partitioning, the aqueous layer was discarded. The organic layer was washed twice each with 2 L of water and concentrated. The residue was treated with 250 mL of CH2Cl2 and stored overnight. A thick precipitate formed overnight. The mixture was filtered and the cake was sucked dry. The cake was dried at 35 C. under house vacuum overnight to afford 24.71 g of the final productproduct. The combined yield was 241 g of the final productproduct. The material showed satisfactory purity and was used in the next step without further purification. 1H NMR 300 MHz, DMSO ppm: 13.53 (s, 1H), 8.35 (q, J=4.7 Hz, 1H), 7.56 (s, 1H), 7.51-7.40 (m, 2H), 7.36-7.23 (m, 3H), 7.13 (dd, J=8.5, 1.3 Hz, 1H), 7.06-7.01 (m, 1H), 2.76 (d, J=4.7 Hz, 3H).

References: [1]Patent: WO2006/48745,2006,A1 .Location in patent: Page/Page column 28-29.
[2]Patent: EP2163544,2010,A1 .Location in patent: Page/Page column 31-32; 22.
[3]Patent: US2006/94881,2006,A1 .Location in patent: Page/Page column 21; 22.

3
[ 261953-36-0 ]
[ 20054-45-9 ]
[ 885126-34-1 ]

Yield	Reaction Conditions	Operation in experiment
65%		Under nitrogen atmosphere 3 kg of 1 -methyl-2-pyrrolidone is mixed with 4.4 kg of 6- iodo-lH-indazole, 7.3 kg of potassium carbonate and 0.17 kg of Copper (II) acetate hydrate at 20-25C. The mixture is heated to 80C. 3.5 kg of 2-mercapto-N-methylbenzamide is mixed with 1.75 kg of l-methyl-2- pyrrolidone and the mixture is heated to 60C. The solution is added to the previously prepared solution of 6-iodo-lH-indazole at 80C in the course of 15 minutes. The mixture is then stirred at 105C for 90 minutes. Then a solution of 8.2 kg of iodine in 2.8 kg of l-methyl-2-pyrrolidone is added. The mixture is stirred at 105C for 120 minutes. Then it is cooled to 80C. 10.7 kg of acetonitrile is added. A mixture of 5 kg of ascorbic acid in 24 kg of water is added in the course of 120 minutes at 80C. Then 24 kg of water is added in the course of 80 minutes at 80C. The resulting mixture is cooled to 0-5C in the course of 4 hours. The mixture is filtered off. Under nitrogen atmosphere the obtained solid is mixed with 20 kg of acetone and 10 kg of water, the mixture is heated to 55-60C and stirred at this temperature for 1 hour. Then the mixture is cooled to 20 C, filtered and the filtered solid is washed with 3 kg of chilled acetone and dried to provide 2-((3-iodo-lH-indazol-6-yl)thio)-N-methylbenzamide in 65% yield and 99% purity (HPLC ES).

References: [1]Patent: WO2020/212253,2020,A1 .Location in patent: Page/Page column 23-24.

Historical Records

Technical Information

Related Functional Groups of
[ 20054-45-9 ]

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[ 20054-45-9 ]

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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