Methanesulfonyl chloride → N-[5-(Benzylsulfanyl)-1,3-thiazol-2-yl]methanesulfonamide
Reaction equation
[NH2:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:5][N:6]=1.[S:15](Cl)([CH3:18])(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:18][S:15]([NH:1][C:2]1[S:3][C:4]([S:7][CH2:8][C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][CH:14]=2)=[CH:5][N:6]=1)(=[O:17])=[O:16]Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 60 °C
Procedure
To a mixture of 2-amino-5-benzylthiothiazole (6.7 g.) and pyridine (50 ml.) was dropwise added mesyl chloride (10.3 g.) over 15 minutes under ice-cooling and stirring, and the mixture was stirred for 3.5 hours at room temperature. After the reaction, the reaction mixture was poured into ice-water (300 ml.), and the precipitates were collected by filtration and then washed with water. The precipitates were added to 1 N sodium hydroxide aqueous solution (50 ml.), and the mixture was heated at 60° C. to produce a solution. The solution was treated with activated carbon and then neutralized. The precipitates were collected by filtration, washed with water and then dried to give powder of 2-methanesulfonamido-5-benzylthiothiazole (7.7 g.), mp 159° to 162° C.
Workup
- customover 15 minutes
- temperaturecooling
- stirringthe mixture was stirred for 3.5 hours at room temperature
- customAfter the reaction
- filtrationthe precipitates were collected by filtration
- washwashed with water
- additionThe precipitates were added to 1 N sodium hydroxide aqueous solution (50 ml.)
- customto produce a solution
- additionThe solution was treated with activated carbon
- filtrationThe precipitates were collected by filtration
- washwashed with water
- customdried
Sources & evidence
- ORD record
- ord-6ec77c4bd1aa4c91bb228b4b2c9de556
- Source dataset
- uspto-grants-1981_03
- Patent number
- US04254260
Reaction notes
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