Diketene → HCID 20534014, compound
Reaction equation
[NH2:1][C:2]1[C:3](=[O:10])[CH:4]=[CH:5][C:6]([Cl:9])=[CH:7][CH:8]=1.[CH2:11]=[C:12]1[O:16][C:14](=[O:15])[CH2:13]1>>[Cl:9][C:6]1[CH:5]=[CH:4][C:3](=[O:10])[C:2]([NH:1][C:14](=[O:15])[CH2:13][C:12](=[O:16])[CH3:11])=[CH:8][CH:7]=1Participants
3
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 2-amino-5-chloro-2,4,6-cycloheptatrien-1-one (1.55 g, described in example 9) and diketene (5 ml) were heated at 100° C. for 1 hr. The mixture was cooled and then purified by chromatography on silica gel using chloroform as the eluant. The appropriate fractions were pooled and the residue was crystallized from diethyl ether to give 650 mg of 1-[(4-chloro-7-oxo-1,3,5-cycloheptatrien-1-yl)amino]-1,3-butanedione, nmr (DMSO-d6) δ2.17 (s, 3H), 3.85 (s, 2H), 7.3 (m, 3H), 8.7 (d, 1H), 10.75 (s, 1H).
Workup
- temperatureThe mixture was cooled
- custom