N,N-Dimethylaniline → HCID 13588338, compound

HRID 280267Notes

Reaction equation

HRID 280267 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][CH2:25][C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)=[CH:20][CH:19]=2)[C:3]=1[C:4]([OH:6])=O.P(Cl)(Cl)(Cl)=O.CN(C)C1C=CC=CC=1>ClCCCl>[Cl:1][C:2]1[C:3]2[C:4](=[O:6])[C:23]3[C:18](=[CH:19][CH:20]=[C:21]([O:24][CH2:25][C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[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 13588353HCID 13588353, compound

Product 1

HCID 13588338HCID 13588338, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 9.7 g of 2-chloro-3,5-dinitro-6-[[4-(phenylmethoxy)phenyl]amino]benzoic acid, 200 ml of 1,2-dichloroethane, 20 ml of phosphorus oxychloride, and 1.0 ml of N,N-dimethylaniline was heated under reflux for 30 minutes. Upon cooling, a solid formed which was collected and washed with 1,2-dichloroethane providing the title compound, mp 217°-220° C.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. temperatureUpon cooling
  4. customa solid formed which
  5. customwas collected
  6. washwashed with 1,2-dichloroethane providing the title compound, mp 217°-220° C.

Sources & evidence

ORD record
ord-0219104bf1e6464f8fca80f2f9b0ea9d
Source dataset
uspto-grants-1986_05
Patent number
US04588730

Reaction notes

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