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

HRID 1399249Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]([O:25]C)=O)=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]21.C([NH2:29])=O.C[O-].[Na+]>CN(C)C=O.[Cl-].[NH4+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:23]([NH2:29])=[O:25])=[C:6]2[C:10]=1[N:9]=[C:8]1[N:11]([C:15]3[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:16]=3[Cl:22])[CH2:12][CH2:13][CH2:14][N:7]21

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of methyl 9-chloro-1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (2.00 g, 4.87 mmol), formamide (1.94 mL, 48.7 mmol) and sodium methoxide (28% solution in methanol, 4.8 mL) in N,N-dimethylformamide (12 mL) was stirred at 120° C. for 19 hr. 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 (1.73 g, 4.37 mmol, 90%) as a pale yellow solid.

Workup

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

Sources & evidence

ORD record: ord-8ea4dc76a1104ce08235b977c18d062f
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08901141B2

Reaction notes

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