Dichloromethane → 2-chloro-N-methyl-5-nitrobenzamide

HRID 1435745Notes

Reaction equation

HRID 1435745 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4](Cl)=[O:5].Cl.CN.ClCCl.[CH2:20]([N:22](CC)CC)C>C(OCC)(=O)C>[Cl:1][C:2]1[CH:10]=[CH:9][C:8]([N+:11]([O-:13])=[O:12])=[CH:7][C:3]=1[C:4]([NH:22][CH3:20])=[O:5]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 117637Benzoyl chloride, 2-chloro-5-nitro-HCID 6364545Methylamine hydrochloride

Product 1

HCID 27951452-chloro-N-methyl-5-nitrobenzamide

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-chloro-5-nitro-benzoyl chloride (502 mg, 2.3 mmol), methylamine hydrochloride (213 mg, 3.1 mmol), dichloromethane (10 ml), and triethylamine (0.84 ml, 6.0 mmol) was stirred for 60 hours. The mixture was treated with ethyl acetate (25 ml). The solution was washed with a mixture of saturated aqueous sodium chloride solution and 1 M hydrochloric acid (1:1, 2×20 ml), washed with aqueous sodium carbonate solution (1 M, 20 ml), dried over sodium sulfate, and concentrated under reduced pressure to provide 2-chloro-N-methyl-5-nitro-benzamide.

Workup

  1. washThe solution was washed with a mixture of saturated aqueous sodium chloride solution and 1 M hydrochloric acid (1:1, 2×20 ml)
  2. washwashed with aqueous sodium carbonate solution (1 M, 20 ml)
  3. dry with materialdried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-39e6f89178bf45799ebf142316df145b
Source dataset
uspto-grants-2009_11
Patent number
US07618968B2

Reaction notes

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