Formamide → 9-Chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamide

HRID 1399273Notes

Reaction equation

HRID 1399273 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]([O:26]C)=O)=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:20]([Cl:21])=[CH:19][C:18]([Cl:22])=[CH:17][C:16]=3[Cl:23])[CH2:12][CH2:13][CH2:14][N:7]21.C([NH2:30])=O.C[O-].[Na+]>CN(C)C=O.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:24]([NH2:30])=[O:26])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[C:16]([Cl:23])=[CH:17][C:18]([Cl:22])=[CH:19][C:20]=3[Cl:21])[CH2:12][CH2:13][CH2:14][N:7]21

Participants

6

Reactant 3

HCID 713FormamideHCID 10942334Sodium MethoxideHCID 57786056HCID 57786056, compound

Product 1

HCID 577860759-Chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamideYield 89.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
60 °C

Procedure

A mixture of methyl 9-chloro-1-(2,4,6-trichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (500 mg, 1.12 mmol), formamide (0.446 mL, 1.20 mmol) and sodium methoxide (28% solution in methanol, 1.1 mL) in N,N-dimethylformamide (5 mL) was stirred at 60° C. for 5 min. The mixture was diluted with aqueous saturated ammonium chloride. The resultant precipitate was collected by filtration, washed with water and diisopropyl ether to give the title compound as a colorless solid (432 mg, 1.00 mmol, 89%).

Workup

  1. filtrationThe resultant precipitate was collected by filtration
  2. washwashed with water and diisopropyl ether

Sources & evidence

ORD record
ord-e98f32db891c4959b455ff1d3ac9eb4b
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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