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

HRID 1282068Notes

Reaction equation

HRID 1282068 reaction equation
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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-3b0bc44afc4b4931bfe11f5b72c32b01
Source dataset
uspto-grants-2002_09
Patent number
US06455528B1

Reaction notes

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