N,N-Dimethylaniline → HCID 13588335, compound

HRID 1731383Notes

Reaction equation

HRID 1731383 reaction equation
[Cl:1][C:2]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][C:8]([N+:14]([O-:16])=[O:15])=[C:7]([NH:17][C:18]2[CH:23]=[CH:22][C:21]([O:24]CC3C=CC(OC)=CC=3)=[CH:20][CH:19]=2)[C:3]=1[C:4](O)=[O:5].P(Cl)(Cl)(Cl)=O.CN(C)C1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[C:3]2[C:4](=[O:5])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([OH:24])[CH:22]=3)[NH:17][C:7]=2[C:8]([N+:14]([O-:16])=[O:15])=[CH:9][C:10]=1[N+:11]([O-:13])=[O:12]

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 13588350HCID 13588350, compound

Product 1

HCID 13588335HCID 13588335, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 5.0 g of 2-chloro-6-[[4-[(4-methoxyphenyl)methoxy]phenyl]amino]-3,5-dinitrobenzoic acid, 10 ml of phosphorus oxychloride, 0.2 ml of N,N-dimethylaniline and 50 ml of 1,2-dichloroethane was heated at reflux for 15 minutes and the reaction mixture was filtered hot. The filter cake was washed with 1,2-dichloroethane to provide the title compound, mp 278°-281° C.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 15 minutes
  3. filtrationthe reaction mixture was filtered hot
  4. washThe filter cake was washed with 1,2-dichloroethane

Sources & evidence

ORD record
ord-ab0ec7f75ff6466fb919f4cd5c30b7c4
Source dataset
uspto-grants-1986_11
Patent number
US04621086

Reaction notes

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