4-Toluenesulfonyl chloride → N-(4-chloromethyl-2-nitrophenylmethyl)acetamide

HRID 1282068노트

반응식

HRID 1282068 반응식
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1.C(N(CC)CC)C.CN(C1C=CC=CN=1)C.C1(C)C=CC(S([Cl:42])(=O)=O)=CC=1>ClCCl.O1CCCC1>[Cl:42][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][NH:10][C:11](=[O:13])[CH3:12])=[C:5]([N+:14]([O-:16])=[O:15])[CH:4]=1

참가 물질

7

반응물 4

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 18423007N-(4-hydroxymethyl-2-nitrophenylmethyl)acetamide

생성물 1

HCID 18423048N-(4-chloromethyl-2-nitrophenylmethyl)acetamide수율 157.4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of N-(4-hydroxymethyl-2-nitrophenylmethyl)acetamide (9.1 g), triethylamine (6.2 ml) and dimethylaminopyridine (0.99 g) in dichloromethane (150 ml)-tetrahydrofuran (50 ml) was added p-toluenesulfonyl chloride (8.5 g) under ice-cooling. This mixture was stirred at room temperature for 3 hr. The reaction mixture was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated to give a yellow oil (15.5 g). The obtained yellow oil was purified by silica gel column chromatography (developing solvent; chloroform:methanol=20:1) to give the title compound (12 g) as a pale-brown solid (7.8 g).

후처리

  1. temperaturecooling
  2. washThe reaction mixture was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-3b0bc44afc4b4931bfe11f5b72c32b01
출처 데이터셋
uspto-grants-2002_09
특허 번호
US06455528B1

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