Hydrochloric Acid → N-[(Benzoylsulfanyl)acetyl]glycine

HRID 2258090Notes

Reaction equation

HRID 2258090 reaction equation
Cl[CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4].[C:10]([OH:18])(=[S:17])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.[OH-].[K+].Cl>C(O)C>[C:10]([S:17][CH2:2][C:3]([NH:5][CH2:6][C:7]([OH:9])=[O:8])=[O:4])(=[O:18])[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 14797Potassium HydroxideHCID 233485N-ChloroacetylglycineHCID 178526132HCID 178526132, compound

Product 1

HCID 53680994N-[(Benzoylsulfanyl)acetyl]glycineYield 98%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To a stirring solution under argon at 0° C. of (1.50g, 10mmoles) N-chloroacetylglycine in (25 mL) ethanol was added (1.41 ml, 12 mmoles) thiobenzoic acid, followed by (7.0 mL, 3N, 21 mmoles) potassium hydroxide over 3 minutes. The reaction was allowed to heat to room temperature for 20 minutes followed by reflux under argon at 50° C. for 2 hours. The reaction was cooled to room temperature and acidified with (5 mL, 2N) hydrochloric acid. The ethanol was rotavapped off to leave N-(S-benzoylmercaptoacetyl)-glycine (m.p. 140.5°-141.5° C.), a white solid, which was washed with water, filtered, and dried in vacuo (2.46g, 98% yield).

Workup

  1. temperatureby reflux under argon at 50° C. for 2 hours
  2. temperatureThe reaction was cooled to room temperature

Sources & evidence

ORD record
ord-aa87c1f200c64189bf9ea8137f9322d9
Source dataset
uspto-grants-1997_08
Patent number
US05659041

Reaction notes

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