Pyridine → N-(Phenylsulfonyl)glycine Methyl Ester
Reaction equation
N1C=CC=CC=1.[C:7]1([S:13](Cl)(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl.[CH3:18][O:19][C:20](=[O:23])[CH2:21][NH2:22]>ClCCl.O>[CH3:18][O:19][C:20]([CH2:21][NH:22][S:13]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[O:15])=[O:14])=[O:23]Participants
Conditions
- Temperature
- 25 °C
Procedure
A 47.5 g (0.6 mol) sample of pyridine was added dropwise to a stirred and cooled (ice bath) slurry of 53.0 g (0.3 mol) benzenesulfonyl chloride and 37.7 g (0.3 mol) glycine methyl ester hydrochloride in 500 ml dichloromethane. The reaction mixture was then allowed to warm to 25° C. and was stirred for about 16 hours. The reaction mixture was diluted with 250 ml water, the organic layer was separated, washed with water, washed with 10% aqueous hydrochloric acid solution, washed with water, dried over magnesium sulfate and evaporated to give 36.5 g N-(methoxycarbonylmethyl)benzenesulfonamide, which crystallized as a colorless solid melting at 62°-63° C. A 3.5 g (0.035 mol) sample of triethylamine was added dropwise to a solution of 8 g (0.035 mol) N-methoxycarbonylmethyl)benzenesulfonamide and 6.5 g (0.035 mol) trichloromethylsulfenyl chloride in 150 ml dichloromethane. The reaction mixture was then stirred at about 25° C. for about 1 hour, washed with water, dried over magnesium sulfate and evaporated to give 7.5 g of N-methoxycarbonylmethyl-N-trichloromethylthiobenzenesulfonamide, which crystallized as a colorless solid melting at 61°-62° C. The compound is tabulated in Table I as Compound No. 1.
Workup
- stirringwas stirred for about 16 hours
- customthe organic layer was separated
- washwashed with water
- washwashed with 10% aqueous hydrochloric acid solution
- washwashed with water
- dry with materialdried over magnesium sulfate
- customevaporated
Sources & evidence
- ORD record
- ord-20ce24710d284dda8d117fb6fe1d3bab
- Source dataset
- uspto-grants-1980_10
- Patent number
- US04230875
Reaction notes
Loading…