Methyl Thioglycolate → Methyl-S-(benzamidomethyl)thioglycolate

HRID 325848노트

반응식

HRID 325848 반응식
[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

참가 물질

6

반응물 4

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

생성물 1

HCID 13314914Methyl-S-(benzamidomethyl)thioglycolate

시약·촉매·용매 1

HCID 1140Toluene용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-ba0ff9f7a54845a7bf6467c6d652ca4e
출처 데이터셋
uspto-grants-1984_04
특허 번호
US04443435

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