Potassium Cyanide → HCID 20434792, compound
Reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.[C-]#N.[K+].O[CH2:27][CH:28]1CC1>>[Cl:1][C:2]1[C:7]2[C:8](=[O:22])[N:9]([CH3:21])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]([O:18][CH2:19][CH:20]3[CH2:28][CH2:27]3)=[O:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1Participants
Procedure
A mixture of 5.0 g (15.6 mmol) of ethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate, 20 ml of hydroxymethyl-cyclopropane and 0.5 g of powdered potassium cyanide is heated to 130° for 18 hours, about 1 ml of solvent being distilled off after 1.3 hours and after 6 hours. The mixture is subseqently evaporated in vacuo and the residue is partitioned between chloroform and water. The chloroform phase is washed three times with water, dried over magnesium sulphate and evaporated. The material obtained is chromatographed on silica gel while eluting with ethyl acetate and subsequently crystallized from ethyl acetate. There is obtained cyclopropylmethyl 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxylate of melting point 194°-195°.
Workup
- temperatureis heated to 130° for 18 hours
- distillationabout 1 ml of solvent being distilled off after 1.3 hours and after 6 hours
- customThe mixture is subseqently evaporated in vacuo
- customthe residue is partitioned between chloroform and water
- washThe chloroform phase is washed three times with water
- dry with materialdried over magnesium sulphate
- customevaporated
- customThe material obtained
- customis chromatographed on silica gel
- washwhile eluting with ethyl acetate
- customsubsequently crystallized from ethyl acetate
Sources & evidence
- ORD record
- ord-19c262e7252b4c9b845676f0e5dccefc
- Source dataset
- uspto-grants-1984_12
- Patent number
- US04489003
Reaction notes
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