2-(Bromoacetyl)-5-chlorothiophene → 1-[(E)-(4-chlorophenyl)methylideneamino]-4-(5-chlorothiophen-2-yl)imidazol-2-amine

HRID 2374664Notes

Reaction equation

HRID 2374664 reaction equation
Br[CH2:2][C:3]([C:5]1[S:6][C:7]([Cl:10])=[CH:8][CH:9]=1)=O.[Cl:11][C:12]1[CH:17]=[CH:16][C:15](/[CH:18]=[N:19]/[NH:20][C:21](=[NH:23])[NH2:22])=[CH:14][CH:13]=1>C(O)C>[Cl:11][C:12]1[CH:13]=[CH:14][C:15](/[CH:18]=[N:19]/[N:20]2[CH:2]=[C:3]([C:5]3[S:6][C:7]([Cl:10])=[CH:8][CH:9]=3)[N:22]=[C:21]2[NH2:23])=[CH:16][CH:17]=1

Participants

4

Reactant 2

HCID 20636342-(Bromoacetyl)-5-chlorothiopheneHCID 178513142DE(2-chloro)-4-chloro-icerguastat

Product 1

HCID 219497541-[(E)-(4-chlorophenyl)methylideneamino]-4-(5-chlorothiophen-2-yl)imidazol-2-amineYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 2-bromo-1-(5-chloro-2-thienyl)-1-ethanone (1.07 g, 4.49 mmol), 2-[(E)-1- (4-chlorophenyl)methylidene]-1-hydrazinecarboximidamide (1.77 g, 8.98 mmol) was heated in ethanol (10 mL) for 2 h, then the mixture was left at room temperature for additional 10 h. The precipitate filtered, washed with hot water, and recrystallized from ethanol to give N1-[(E)-1-(4-chlorophenyl)methylidene]-4-(5-chloro-2-thienyl)-1H-1,2-imidazolediamine 2 (1.09 g, 72%) as a brown solid.

Workup

  1. filtrationThe precipitate filtered
  2. washwashed with hot water
  3. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-aa5aa84886cf41e1bd70a001bb3e6e44
Source dataset
uspto-grants-2008_12
Patent number
US07462723B2

Reaction notes

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