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2,3-Dichloroaniline → N-(2,3-dichlorophenyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide

HRID 1428992
Notes
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Reaction equation

HRID 1428992 reaction equation
[CH3:1][C:2]1[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]([CH3:10])=[C:5]([C:7]([OH:9])=O)[N:6]=1.C(Cl)(=O)C(Cl)=O.C(N(C(C)C)CC)(C)C.[Cl:32][C:33]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:34]=1[NH2:35]>C(Cl)(Cl)Cl.ClCCl>[Cl:32][C:33]1[C:39]([Cl:40])=[CH:38][CH:37]=[CH:36][C:34]=1[NH:35][C:7]([C:5]1[N:6]=[C:2]([CH3:1])[N:3]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[C:4]=1[CH3:10])=[O:9]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 118442,3-DichloroanilineHCID 65578Oxalyl chlorideHCID 81531DiisopropylethylamineHCID 545792222,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid

Product 1

HCID 58695755N-(2,3-dichlorophenyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamideYield 36%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolvent
HCID 6344DichloromethaneSolvent

Procedure

Part A: To a magnetically stirred suspension of 2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxylic acid (0.4 gram, 1.85 mmol) in CHCl3 (4 ml) was added oxalyl chloride (0.34 gram, 2.685 mmol) and the resulting mixture was reacted at 58° C. for 2 hours and subsequently concentrated in vacuo. The resulting residue was taken up in dichloromethane and diisopropylethylamine (0.28 gram, 2.148 mmol) was subsequently added. A solution of 2,3-dichloroaniline (0.35 gram, 2.146 mmol) in dichloromethane (5 ml) was slowly added to the resulting mixture and the resulting mixture was reacted for 2 hours at room temperature and subsequently concentrated in vacuo. The resulting residue was purified by flash chromatography (dichloromethane) to give N-(2,3-dichlorophenyl)-2,5-dimethyl-1-phenyl-1H-imidazole-4-carboxamide (0.24 gram, 36% yield). Melting point: 127-129° C.

Workup

  1. customthe resulting mixture was reacted at 58° C. for 2 hours
  2. concentrationsubsequently concentrated in vacuo
  3. customthe resulting mixture was reacted for 2 hours at room temperature
  4. concentrationsubsequently concentrated in vacuo
  5. customThe resulting residue was purified by flash chromatography (dichloromethane)

Sources & evidence

ORD record
ord-f0e7725abe794beb85a5373c25be010c
Source dataset
uspto-grants-2015_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08937184B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes