Methanethiol → HCID 152460, compound

HRID 1600359Notes

Reaction equation

HRID 1600359 reaction equation
[OH-].[Na+].[Na].[CH3:4][SH:5].CS.[Na].[C:9]1([NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2Cl)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1>O>[C:9]1([NH:15][C:16](=[O:24])[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[S:5][CH3:4])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

7

Reactant 5

HCID 878MethanethiolHCID 14798Sodium HydroxideHCID 232652-ChlorobenzanilideHCID 5360545SodiumHCID 45051789Methylmercaptan sodium

Product 1

HCID 152460HCID 152460, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a 500 ml four-necked flask equipped with a stirrer, a thermometer, and acondenser, 46.3 g (0.2 mol) of N-phenyl-2-chlorobenzamide obtained in Production Example 1, 100 g of toluene, and 9.3 g of an aqueous solution of 50% by weight tetra-n-butylammonium bromide are placed. Separately, 12.0 g (0.30 mol) of sodium hydroxide and 113.7 g of water are placed intoanother container under a nitrogen gas atmosphere, and 14.5 g (0.30 mol) ofmethanethiol are added to the above mixture at room temperature over about 1 hour to prepare 140.2 g of sodium salt solution of methanethiol. 140.2 g(0.3 mol) of the aqueous solution of sodium methyl mercaptan thus prepared is added to the mixture containing N-phenyl-2-chlorobenzamide described above at 80° C. while stirring, to be allowed to react with each other under reflux for 1 hour. After completion of the reaction, the reaction mixture is cooled to room temperature to precipitate white crystals, which are washed with water and then with toluene and dried, to give 46.2 g of N-phenyl-2-(methylthio)benzamide (melting point 148°to 149° C.). The yield of the product against N-phenyl-2-chlorobenzamide is 95%.

Workup

  1. addition14.5 g (0.30 mol) ofmethanethiol are added to the above mixture at room temperature over about 1 hour
  2. additionis added to the mixture
  3. customdescribed above at 80° C.
  4. customto react with each other
  5. temperatureunder reflux for 1 hour
  6. customAfter completion of the reaction
  7. customto precipitate white crystals, which
  8. washare washed with water
  9. dry with materialwith toluene and dried

Sources & evidence

ORD record
ord-06f98a87e81444308eb10173bde9aac7
Source dataset
uspto-grants-1998_04
Patent number
US05744609

Reaction notes

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