N,N-Dimethylaniline → HCID 13588229, compound

HRID 1248832Notes

Reaction equation

HRID 1248832 reaction equation
Cl[C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[C:7]([Cl:14])[C:3]=1[C:4]([OH:6])=[O:5].[CH2:15]([O:22][C:23]1[CH:29]=[CH:28][C:26]([NH2:27])=[CH:25][CH:24]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.CN(C)C1C=CC=CC=1>>[Cl:14][C:7]1[CH:8]=[CH:9][C:10]([N+:11]([O-:13])=[O:12])=[C:2]([NH:27][C:26]2[CH:25]=[CH:24][C:23]([O:22][CH2:15][C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:29][CH:28]=2)[C:3]=1[C:4]([OH:6])=[O:5]

Participants

4

Reactant 3

HCID 949N,N-DimethylanilineHCID 228604-BenzyloxyanilineHCID 3506232,6-Dichloro-3-nitrobenzoic acid

Product 1

HCID 13588229HCID 13588229, compound

Procedure

A mixture of 50.0 g of 2,6-dichloro-3-nitrobenzoic acid, 85.7 g of 4-benzyloxyaniline, and 115 ml of N,N-dimethylaniline was heated on a steam bath for 24 hours. The cooled mixture was triturated with 600 ml of chloroform and filtered. The precipitate was stirred in a mixture of 350 ml of chloroform and 350 ml of 1N aq NaOH. The red sodium salt was collected and stirred with a mixture of 300 ml of 1N hydrochloric acid and 1.5 l of chloroform. The chloroform layer was concentrated to provide the title compound as red crystals, mp 172°-174° C.

Workup

  1. temperaturewas heated on a steam bath for 24 hours
  2. customThe cooled mixture was triturated with 600 ml of chloroform
  3. filtrationfiltered
  4. customThe red sodium salt was collected
  5. stirringstirred with a mixture of 300 ml of 1N hydrochloric acid and 1.5 l of chloroform
  6. concentrationThe chloroform layer was concentrated

Sources & evidence

ORD record
ord-9bf6fc4cb06449628ed53dfda8ac8971
Source dataset
uspto-grants-1986_12
Patent number
US04626540

Reaction notes

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