Triethylamine → 1-[2-(4-Chloroanilino)anilino]-3-fluoro-4,6-dinitrobenzene

HRID 1019847Notes

Reaction equation

HRID 1019847 reaction equation
[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH2:9])=[CH:4][CH:3]=1.[F:16][C:17]1[C:22]([N+:23]([O-:25])=[O:24])=[CH:21][C:20]([N+:26]([O-:28])=[O:27])=[C:19](F)[CH:18]=1.C(N(CC)CC)C>CO>[Cl:1][C:2]1[CH:15]=[CH:14][C:5]([NH:6][C:7]2[CH:13]=[CH:12][CH:11]=[CH:10][C:8]=2[NH:9][C:19]2[C:20]([N+:26]([O-:28])=[O:27])=[CH:21][C:22]([N+:23]([O-:25])=[O:24])=[C:17]([F:16])[CH:18]=2)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 675981,5-Difluoro-2,4-dinitrobenzeneHCID 522323N-(4-chlorophenyl)benzene-1,2-diamine

Product 1

HCID 715038811-[2-(4-Chloroanilino)anilino]-3-fluoro-4,6-dinitrobenzene

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The solid from step B was added to a solution of 1,3-difluoro-4,6-dinitrobenzene (46 g) in methanol (200 mL), then triethylamine (31.4 mL) was added, and stirred at rt for 4 h. The reaction mixture was filtered, and the cake was washed with methanol to give 80.6 g of red solid.

Workup

  1. filtrationThe reaction mixture was filtered
  2. washthe cake was washed with methanol

Sources & evidence

ORD record
ord-a0b26f8a19b44080a56c6d12186e3245
Source dataset
uspto-grants-2014_05
Patent number
US08716292B2

Reaction notes

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