Water → N-(3,4-dichlorophenyl)-2-chloro-3-nitro-5-trifluoromethylbenzamide

HRID 550348Notes

Reaction equation

HRID 550348 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].CC(C)=O.O.[Cl:15][C:16]1[C:24]([N+:25]([O-:27])=[O:26])=[CH:23][C:22]([C:28]([F:31])([F:30])[F:29])=[CH:21][C:17]=1[C:18](Cl)=[O:19].O>CC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:18](=[O:19])[C:17]2[CH:21]=[C:22]([C:28]([F:31])([F:30])[F:29])[CH:23]=[C:24]([N+:25]([O-:27])=[O:26])[C:16]=2[Cl:15])[CH:6]=[CH:7][C:8]=1[Cl:9]

Participants

6

Reactant 4

HCID 962WaterHCID 72573,4-DichloroanilineHCID 18366337Propan-2-one--water (1/1)HCID 200341672-Chloro-3-nitro-5-trifluoromethylbenzoyl chloride

Product 1

HCID 86620253N-(3,4-dichlorophenyl)-2-chloro-3-nitro-5-trifluoromethylbenzamideYield 93.9%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of 3,4-dichloroaniline (2.6 g; 2 eq.) in a 1/1 acetone/water mixture (30 ml) is added dropwise at 0° C. a solution of 2-chloro-3-nitro-5-trifluoromethylbenzoyl chloride (2.3 g; 1 eq.) in acetone (10 ml). After 18 hours at room temperature, 20 ml of water are added. The resulting solid is filtered off by suction, washed with water and dried. 3.1 g of N-(3,4-dichlorophenyl)-2-chloro-3-nitro-5-trifluoromethylbenzamide are obtained (m.p.=202° C.).

Workup

  1. filtrationThe resulting solid is filtered off by suction
  2. washwashed with water
  3. customdried

Sources & evidence

ORD record
ord-77886a0aee534ac6bbc5007fff8fcc9a
Source dataset
uspto-grants-2011_05
Patent number
US07947675B2

Reaction notes

Loading…