Water → 12-oxo-3,4,6,12-tetrahydro-1H-thiopyrano[4',3':4,5]pyrido[1,2-a]benzimidazole-5-carbonitrile
Reaction equation
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[CH2:10][C:11]#[N:12].O=[C:14]1[CH2:19][CH2:18][S:17][CH2:16][CH:15]1[C:20](OC)=[O:21].C([O-])(=O)C.[NH4+].O>C(#N)C>[O:21]=[C:20]1[N:3]2[C:2]([NH:1][C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=32)=[C:10]([C:11]#[N:12])[C:14]2[CH2:19][CH2:18][S:17][CH2:16][C:15]1=2Participants
6
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 140 °C
Procedure
A mixture of 1H-benzimidazol-2-ylacetonitrile (13 g), methyl 4-oxotetrahydro-2H-thiopyran-3-carboxylate (15.3 g), and ammonium acetate (33 g) was heated and stirred at 140° C. for 1 hour. The reaction mixture was cooled to room temperature, water and acetonitrile were added, and the resulting precipitate was collected by filtration and dried under reduced pressure to obtain 12-oxo-3,4,6,12-tetrahydro-1H-thiopyrano[4′,3′:4,5]pyrido[1,2-a]benzimidazole-5-carbonitrile (16 g).
Workup
- temperaturewas heated
- temperatureThe reaction mixture was cooled to room temperature
- filtrationthe resulting precipitate was collected by filtration
- customdried under reduced pressure
Sources & evidence
- ORD record
- ord-1911c51393d64009890652cfd444e22a
- Source dataset
- uspto-grants-2014_09
- Patent number
- US08822688B2
Reaction notes
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