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

HRID 1399022Notes

Reaction equation

HRID 1399022 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([C:22](OC)=[O:23])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1.C([NH2:28])=O.C[O-].[Na+].CN(C)C=O>[Cl-].[NH4+]>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[N:9]1[C:14]2=[N:15][C:16]3[C:17](=[C:18]([C:22]([NH2:28])=[O:23])[CH:19]=[CH:20][CH:21]=3)[N:13]2[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 713FormamideHCID 6228DimethylformamideHCID 10942334Sodium MethoxideHCID 57786230Methyl 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate

Product 1

HCID 577857971-(2,4-Dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxamideYield 83%

Reagents, catalysts & solvents 1

HCID 25517Ammonium ChlorideSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of methyl 1-(2,4-dichlorophenyl)-1,2,3,4-tetrahydropyrimido[1,2-a]benzimidazole-6-carboxylate (Example 81; 350 mg, 0.930 mmol), formamide (3.0 mL), and sodium methoxide (28% solution in methanol, 1.0 mL), and N,N-dimethylformamide (3.0 mL) was stirred at 120° C. for 20 hr. The mixture was diluted with aqueous saturated ammonium chloride, and the precipitate was collected by filtration, washed with water, washed with diisopropyl ether to give the title compound as a colorless powder (280 mg, 0.775 mmol, 83%).

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. washwashed with diisopropyl ether

Sources & evidence

ORD record
ord-e932b47127aa4ebf954c3742d06adb8a
Source dataset
uspto-grants-2014_12
Patent number
US08901141B2

Reaction notes

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