Methyl chloroformate → HCID 12884281, compound

HRID 1729938Notes

Reaction equation

ClC(OC)=O.C(N(CC)CC)C.[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([NH:20][C:21]([C:23]2[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=2[C:29]([OH:31])=[O:30])=O)=[C:16]([F:32])[CH:15]=1>C(Cl)Cl>[Cl:13][C:14]1[CH:19]=[CH:18][C:17]([N:20]=[C:21]2[C:23]3[CH2:28][CH2:27][CH2:26][CH2:25][C:24]=3[C:29](=[O:31])[O:30]2)=[C:16]([F:32])[CH:15]=1

Participants

Conditions

Temperature: 0 °C

Procedure

1.59 Parts of methyl chloroformate was added dropwise during 15 minutes to a stirred solution of 1.87 parts of triethylamine and 5 parts of 2-(4-chloro-2-fluorophenylaminocarbonyl)-1-cyclohexene-1-carboxylic acid in 200 parts of methylene chloride cooled to 0° C. The reaction mixture was allowed to come to ambient temperature during 1 hour after which it was washed successively with 100 parts of water (twice) and 100 parts of a saturated aqueous sodium chloride solution. After drying with anhydrous sodium sulfate, the solution was evaporated under reduced pressure of 300 mm. Hg at 25° C to 5.6 parts of a yellow semisolid. Analysis of the semisolid by high pressure liquid chromatography indicates the presence of 3-(4-chloro-2-fluorophenylimino)-4,5,6,7-tetrahydro-1-(3H)-isobenzofuranone in 51% concentration.

Workup

washafter which it was washed successively with 100 parts of water (twice) and 100 parts of a saturated aqueous sodium chloride solution
dry with materialAfter drying with anhydrous sodium sulfate
customthe solution was evaporated under reduced pressure of 300 mm. Hg at 25° C to 5.6 parts of a yellow semisolid
concentrationin 51% concentration

Sources & evidence

ORD record: ord-97854b40861b44feb297029342dda828
Source dataset: uspto-grants-1976_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03990880

Reaction notes

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