Triethylamine → N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide

HRID 1352659Notes

Reaction equation

HRID 1352659 reaction equation
[CH2:1]([O:3][C:4]1[CH:12]=[C:11]([C:13]#[N:14])[CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])[CH3:2].[Cl:15][C:16]1[C:21]([Cl:22])=[CH:20][C:19]([NH2:23])=[C:18]([NH2:24])[CH:17]=1.C(N(CC)CC)C>ClCCl>[NH2:24][C:18]1[CH:17]=[C:16]([Cl:15])[C:21]([Cl:22])=[CH:20][C:19]=1[NH:23][C:6](=[O:7])[C:5]1[CH:9]=[CH:10][C:11]([C:13]#[N:14])=[CH:12][C:4]=1[O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 211007434-Cyano-2-ethoxybenzoyl chloride

Product 1

HCID 21101176N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamideYield 104.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-ethoxy-4-cyanobenzoyl chloride (10.9 g, 52 mmol), prepared as in Preparation 11, in dichloromethane (109 ml) was added dropwise in 5 h to a solution of 4,5-dichlorophenylendiamine (18.5 g, 104.5 mmol) and triethylamine (53 g=72.6 ml, 523 mmol) in dichloromethane (550 ml). Stirring was continued for additional 2 h. The solvent was removed under vacuum and the residue was triturated with water (100 ml), filtered and dried at 50° C. under vacuum. The solid was suspended in diethyl ether (200 ml), stirred for 1 h, filtered and dried under vacuum to give 19 g of N-(2-amino-4,5-dichlorophenyl)-2-ethoxy-4-cyanobenzamide (yield 51%), mp=195–198° C.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with water (100 ml)
  3. filtrationfiltered
  4. customdried at 50° C. under vacuum
  5. stirringstirred for 1 h
  6. filtrationfiltered
  7. customdried under vacuum

Sources & evidence

ORD record
ord-24cf7191820048498692652b457e64c5
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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