Carbon Tetrachloride → 7-Methyl-4-chromanon-8-ylisocyanate

HRID 1900039Notes

Reaction equation

HRID 1900039 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[C:10]([CH3:20])=[CH:11][CH:12]=[C:13]2[C:18]=1[O:17][CH2:16][CH2:15][C:14]2=[O:19].Cl[C:22](Cl)([O:24]C(=O)OC(Cl)(Cl)Cl)Cl.C(Cl)(Cl)(Cl)Cl>CCOCC>[CH3:20][C:10]1[C:9]([N:8]=[C:22]=[O:24])=[C:18]2[C:13]([C:14](=[O:19])[CH2:15][CH2:16][O:17]2)=[CH:12][CH:11]=1

Participants

6

Reactant 4

HCID 5943Carbon TetrachlorideHCID 8471TriethylamineHCID 94429TriphosgeneHCID 10352232HCID 10352232, compound

Product 1

HCID 233719147-Methyl-4-chromanon-8-ylisocyanateYield 276.5%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

0.15 ml of triethylamine was added to a mixture of 180 mg of 8-amino-7-methyl-4-chromanone, 103 mg of triphosgene and 8 ml of carbon tetrachloride at room temperature with stirring, and the reaction was allowed to proceed under reflux for 6.5 hr. The reaction mixture was cooled to room temperature, ether was added thereto, and insolubles were removed by filtration. The filtrate was concentrated to give 195 mg of the intended title compound.

Workup

  1. temperatureunder reflux for 6.5 hr
  2. custominsolubles were removed by filtration
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-49254eb93c7b4dc590fd26488b3a75fa
Source dataset
uspto-grants-1996_11
Patent number
US05574061

Reaction notes

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