Methyl Thioglycolate → Methyl-S-(benzamidomethyl)thioglycolate

HRID 325848Notes

Reaction equation

HRID 325848 reaction equation
[C:1]([O:5][CH3:6])(=[O:4])[CH2:2][SH:3].ClC[C:9]1[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=1[C:11]([NH2:13])=[O:12].[CH3:18]COC(C)=O.C(Cl)Cl.[K+].[Br-]>C1(C)C=CC=CC=1>[CH3:6][O:5][C:1](=[O:4])[CH2:2][S:3][CH2:18][NH:13][C:11](=[O:12])[C:10]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:9]=1

Participants

6

Reactant 4

HCID 16907Methyl ThioglycolateHCID 253877Potassium BromideHCID 21226138Dichloromethane ethylacetateHCID 222911382-(Chloromethyl)benzamide

Product 1

HCID 13314914Methyl-S-(benzamidomethyl)thioglycolate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl thioglycolate (2 g, 18.84 mmol) and chloromethylbenzamide (3.2 g, 18.84 mmol) was dissolved in 60 ml of dry toluene, and the clear solution was stirred for 18 hours at 25° C. under nitrogen at which time a TLC (10% EtOAc/CH2Cl2) showed that the reaction was complete. Solid materials were removed by filtration and the toluene was evaporated to give a pale yellow oil. Purification on silica gel (10% EtOAc/CH2Cl2) yielded a colorless oil that solidified on standing: mp 65°-68° C.; IR (KBr) 3280, 1730, 1620 cm-1 ; NMR (CDCl3) δ7.98-7.25 (m, 5, aryl), 4.77 (d, 2, --SCH2NH--), 3.77 (s, 3, --OCH3), 3.43 (s, 2, --SCH2C=O).

Workup

  1. customSolid materials were removed by filtration
  2. customthe toluene was evaporated
  3. customto give a pale yellow oil
  4. customPurification on silica gel (10% EtOAc/CH2Cl2)
  5. customyielded a colorless oil that

Sources & evidence

ORD record
ord-ba0ff9f7a54845a7bf6467c6d652ca4e
Source dataset
uspto-grants-1984_04
Patent number
US04443435

Reaction notes

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