Water → HCID 19001542, compound

HRID 2259633Notes

Reaction equation

HRID 2259633 reaction equation
[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:13])([F:12])[F:11])=[CH:6][C:4]=1[NH2:5].[H-].[Na+].Cl[C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:25])[F:24])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28].O>CN(C)C=O>[CH3:1][O:2][C:3]1[CH:9]=[CH:8][C:7]([C:10]([F:11])([F:12])[F:13])=[CH:6][C:4]=1[NH:5][C:17]1[CH:22]=[CH:21][C:20]([C:23]([F:26])([F:24])[F:25])=[CH:19][C:18]=1[N+:27]([O-:29])=[O:28]

Participants

6

Reactant 4

HCID 962WaterHCID 84624-Chloro-alpha,alpha,alpha-trifluoro-3-nitrotoluene2×HCID 24758Sodium hydride3×HCID 6006372-Methoxy-5-(trifluoromethyl)aniline

Product 1

HCID 19001542HCID 19001542, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To an ice cooled solution of 2-Methoxy-5-trifluoromethylaniline (311 mmol, 59.4 g) in 500 ml dry dimethylformamide is added sodiumhydride (438 mmol, 17.5 g 60%) followed by slow addition of 2-chloro-5-trifluoromethyl-nitrobenzene (311 mmol, 47.4 ml) and the mixture is stirred for 60 hours. More sodiumhydride (10 g 60%) is added and after stirring for additional two hours is another portion of 2-chloro-5-trifluoromethyl-nitrobenzene (5 ml) and sodiumhydride (2 g 60%) added. Upon completion is the reaction mixture poured into water and a black precipitate is formed. The crude product is filtered of and is washed with 1M HCl and petroleum ether yielding the title compound as grey crystals, M.p. 86°-88° C.

Workup

  1. stirringafter stirring for additional two hours
  2. additionadded
  3. customa black precipitate is formed
  4. filtrationThe crude product is filtered of and
  5. washis washed with 1M HCl and petroleum ether yielding the title compound as grey crystals, M.p. 86°-88° C.

Sources & evidence

ORD record
ord-7a13eead76d94702bc24bcbe9366e144
Source dataset
uspto-grants-1995_12
Patent number
US05475015

Reaction notes

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