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Dimethylformamide → n-(4-Dimethylaminobenzyl)-2-nitro-4-trifluoromethylaniline

HRID 636681
Notes
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Reaction equation

HRID 636681 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=1[N+:12]([O-:14])=[O:13].Cl.Cl.[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH2:24])=[CH:21][CH:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:17][N:18]([CH3:27])[C:19]1[CH:26]=[CH:25][C:22]([CH2:23][NH:24][C:2]2[CH:7]=[CH:6][C:5]([C:8]([F:11])([F:10])[F:9])=[CH:4][C:3]=2[N+:12]([O-:14])=[O:13])=[CH:21][CH:20]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotolueneHCID 11430Potassium CarbonateHCID 27346334-(aminomethyl)-N,N-dimethylaniline dihydrochloride

Product 1

HCID 8461356n-(4-Dimethylaminobenzyl)-2-nitro-4-trifluoromethylaniline

Reagents, catalysts & solvents 1

HCID 962
Water
Solvent

Procedure

A mixture of 4-chloro-3-nitrobenzotrifluoride (5.05 g, 22.4 mmol), 4-(dimethylamino)benzylamine dihydrochloride (5.0 g, 22.4 mmol), potassium carbonate (9.29 g, 76.2 mmol) and dimethylformamide (60 ml) was stirred at room temperature for 3 days. Water (60 ml) was added and the mixture was stirred for 0.5 h followed by filtration. The crystalline product was triturated with petroleum ether. Yield 6.08 g, 80%. M.p. 158-160° C.

Workup

  1. stirringthe mixture was stirred for 0.5 h
  2. filtrationfollowed by filtration
  3. customThe crystalline product was triturated with petroleum ether

Sources & evidence

ORD record
ord-421e2cf25b7b48ad9f177e4e3a3d3315
Source dataset
uspto-grants-2001_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06194447B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes