Pyridine → N-(Phenylsulfonyl)glycine Methyl Ester

HRID 894330Notes

Reaction equation

HRID 894330 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

6

Reactant 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 5149288N-(Phenylsulfonyl)glycine Methyl EsterYield 53.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

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.

Workup

  1. stirringwas stirred for about 16 hours
  2. customthe organic layer was separated
  3. washwashed with water
  4. washwashed with 10% aqueous hydrochloric acid solution
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. customevaporated

Sources & evidence

ORD record
ord-268212491fbe4db9a3fb80ad7e46ffa3
Source dataset
uspto-grants-1981_08
Patent number
US04283416

Reaction notes

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