Acetone Cyanohydrin → HCID 19898130, compound
Reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1.C(N(CC)CC)C.[CH2:21]([S:23][CH:24]([CH3:39])[CH2:25][CH:26]1[CH:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:30](=[O:37])[CH2:29][C:28](=[O:38])[CH2:27]1)[CH3:22].CC(C)(O)C#N>ClCCl>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([CH:29]2[C:28](=[O:38])[CH2:27][CH:26]([CH2:25][CH:24]([S:23][CH2:21][CH3:22])[CH3:39])[CH:31]([C:32]([O:34][CH2:35][CH3:36])=[O:33])[C:30]2=[O:37])=[O:7])=[C:4]([N+:11]([O-:13])=[O:12])[CH:3]=1Participants
Procedure
A solution of 4-chloro-2-nitrobenzoyl chloride (1 g) in dry dichloromethane (5 ml) was added at 0°-10° C. to a stirred solution of triethylamine (0.62 ml) and 5-(2-ethylthiopropyl)-6-carbethoxycyclohexane-1,3-dione (1.3 g) in dry dichloromethane (20 ml) and the mixture stirred at ambient temperature for 2 hours. Triethylamine (1.9 g) and acetone cyanohydrin (0.1 ml) were added successively to the solution and the mixture stirred at ambient temperature for a further 18 hours. The mixture was washed successively with 2N hydrochloric acid (10 ml) and water (2×10 ml) dried over magnesium sulphate and evaporated under reduced pressure to give 2-(4-chloro-2-nitrobenzoyl)-5-(2-ethylthiopropyl)-6-carbethoxycyclohexane-1,3-dione (0.6 g), mp 102°-104° C., as an orange crystalline solid.
Workup
- stirringthe mixture stirred at ambient temperature for a further 18 hours
- washThe mixture was washed successively with 2N hydrochloric acid (10 ml) and water (2×10 ml)
- dry with materialdried over magnesium sulphate
- customevaporated under reduced pressure
Sources & evidence
- ORD record
- ord-1c6285c5a5a34e60afa9183f70c71bd1
- Source dataset
- uspto-grants-1992_05
- Patent number
- US05114461
Reaction notes
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