Phenyl chloroformate → HCID 20458270, compound

HRID 544551Notes

Reaction equation

HRID 544551 reaction equation
Cl[C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3].[CH2:11]([O:13][C:14]([C:16]1[C:17]([CH3:40])=[C:18]2[C:23](=[CH:24][C:25]=1[CH3:26])[N:22]=[C:21]([CH2:27][OH:28])[N:20]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([F:38])([F:37])[F:36])[C:19]2=[O:39])=[O:15])[CH3:12]>N1C=CC=CC=1>[CH2:11]([O:13][C:14]([C:16]1[C:17]([CH3:40])=[C:18]2[C:23](=[CH:24][C:25]=1[CH3:26])[N:22]=[C:21]([CH2:27][O:28][C:2]([O:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=[O:3])[N:20]([C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[C:35]([F:38])([F:37])[F:36])[C:19]2=[O:39])=[O:15])[CH3:12]

Participants

4

Reactant 2

HCID 15891Phenyl chloroformateHCID 20458300HCID 20458300, compound

Product 1

HCID 20458270HCID 20458270, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
80 °C

Procedure

Phenyl chloroformate (470 mg) was added to a solution of 420 mg of 6-ethoxycarbonyl-2-hydroxymethyl-5,7-dimethyl-3-[2-(trifluoromethyl)phenyl]-4(3H)-quinazolinone in 5 ml of pyridine. The reaction mixture was stirred at 80° C. for 3 hours, and the solvent was then evaporated off in vacuo. The residue was taken up with ethyl acetate, and the solution was washed successively with 1N aqueous hydrochloric acid and water, and dried over anhydrous sodium sulfate. The ethyl acetate was evaporated off to give 400 mg of crude 6-ethoxycarbonyl-5,7-dimethyl-2-(phenoxycarbonyloxymethyl)-3-[2-(trifluoromethyl)phenyl]-4(3H)-quinazolinone.

Workup

  1. customthe solvent was then evaporated off in vacuo
  2. washthe solution was washed successively with 1N aqueous hydrochloric acid and water
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe ethyl acetate was evaporated off

Sources & evidence

ORD record
ord-2d06fce5ed5e44f9b0bc1d8b018a876f
Source dataset
uspto-grants-1984_05
Patent number
US04451467

Reaction notes

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