Diketene → HCID 20534014, compound

HRID 1156825Notes

Reaction equation

HRID 1156825 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]=1

Participants

3

Reactant 2

HCID 12661DiketeneHCID 12557673HCID 12557673, compound

Product 1

HCID 20534014HCID 20534014, compound

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

  1. temperatureThe mixture was cooled
  2. custompurified by chromatography on silica gel
  3. customthe residue was crystallized from diethyl ether

Sources & evidence

ORD record
ord-26a39316d38249cb925e9e007aff87e0
Source dataset
uspto-grants-1982_06
Patent number
US04337265

Reaction notes

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