Reaction equation
CS(O)(=O)=O.OCCCN1[C:14]2[CH:15]=[CH:16][C:17]([CH3:19])=[CH:18][C:13]=2NC1=O.[C:21]1(N2C3(CCNCC3)C(=O)NC2)[CH:26]=CC=C[CH:22]=1.C(=O)([O-])[O-:39].[Na+].[Na+]>CN(C)C=O>[CH3:22][CH2:21][CH2:26][C:18](=[O:39])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH3:19]Participants
Conditions
- Temperature
- 60 °C
Procedure
A mixture of 5.68 parts of 1,3-dihydro-1-(3-hydroxypropyl)-5-methyl-2H-benzimidazol-2-one methanesulfonate, 4.62 parts of 1-phenyl-1,3,8-triazaspiro[4,5]decan-4-one, 3.7 parts of sodium carbonate and 45 parts of N,N-dimethylformamide is stirred for 1 hour at 60° C. The reaction mixture is cooled and poured onto water. The precipitated product is filtered off and purified by column-chromatography over silica gel using a mixture of trichloromethane and 10% of methanol as eluent. The pure fractions are collected and the eluent is evaporated. The residue is crystallized from a mixture of N,N-dimethylformamide and water, yielding 2 parts (24%) of 8-[3-(1,3-dihydro-5-methyl-2-oxo-2H-benzimidazol-1-yl)propyl]-1-phenyl-1,3,8-triazaspiro[4,5[decan-4-one; mp. 255.5° C.
Workup
- temperatureThe reaction mixture is cooled
- additionpoured onto water
- filtrationThe precipitated product is filtered off
- custompurified by column-chromatography over silica gel using
- additiona mixture of trichloromethane and 10% of methanol as eluent
- customThe pure fractions are collected
- customthe eluent is evaporated
- customThe residue is crystallized from a mixture of N,N-dimethylformamide and water
Sources & evidence
- ORD record
- ord-847461700ade486b97da49aa5ea301e7
- Source dataset
- uspto-grants-1979_07
- Patent number
- US04160836
Linked notes
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