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

HRID 1352652Notes

Reaction equation

HRID 1352652 reaction equation
[CH3:1][O:2][C:3]1[CH:11]=[C:10]([C:12]#[N:13])[CH:9]=[CH:8][C:4]=1[C:5](Cl)=[O:6].[Cl:14][C:15]1[C:20]([Cl:21])=[CH:19][C:18]([NH2:22])=[C:17]([NH2:23])[CH:16]=1.C(N(CC)CC)C>ClCCl>[NH2:23][C:17]1[CH:16]=[C:15]([Cl:14])[C:20]([Cl:21])=[CH:19][C:18]=1[NH:22][C:5](=[O:6])[C:4]1[CH:8]=[CH:9][C:10]([C:12]#[N:13])=[CH:11][C:3]=1[O:2][CH3:1]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 792974,5-Dichloro-1,2-phenylenediamineHCID 226750494-Cyano-2-methoxybenzoyl chloride

Product 1

HCID 21101177N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamideYield 86.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-methoxy-4-cyanobenzoyl chloride (2 g, 10 mmol) in dichloromethane (20 ml) was added dropwise in 1 h to a solution of 4,5-dichlorophenylendiamine (3.54 g, 20 mmol) and triethylamine (10.1 g=13.9 ml, 100 mmol) in dichloromethane (20 ml). Stirring was continued for additional two hours. The solvent was removed under vacuum and the residue was triturated with water (50 ml), filtered and dried at 50° C. under vacuum. The solid was suspended in diethyl ether (150 ml), stirred for 1 h, filtered and dried under vacuum to give 2.9 g of N-(2-amino-4,5-dichlorophenyl)-2-methoxy-4-cyanobenzamide (yield 43%), mp>250° C.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with water (50 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-ded22f44dbe0478798e9caf097d87fec
Source dataset
uspto-grants-2007_05
Patent number
US07220769B2

Reaction notes

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