Methyl Thioglycolate → Methyl-S-(benzamidomethyl)thioglycolate

HRID 325848ノート

反応式

HRID 325848 の反応式
[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

参加物

6

反応物 4

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

生成物 1

HCID 13314914Methyl-S-(benzamidomethyl)thioglycolate

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-ba0ff9f7a54845a7bf6467c6d652ca4e
出典データセット
uspto-grants-1984_04
特許番号
US04443435

反応ノート

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