HCID 20541555, compound → HCID 12884281, compound

HRID 1729937Notes

Reaction equation

HRID 1729937 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([C:11]2[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=2[C:17]([OH:19])=[O:18])=O)=[C:4]([F:20])[CH:3]=1>O1CCOCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]2[C:11]3[CH2:16][CH2:15][CH2:14][CH2:13][C:12]=3[C:17](=[O:19])[O:18]2)=[C:4]([F:20])[CH:3]=1

Participants

3

Reactant 1

HCID 20541555HCID 20541555, compound

Product 1

HCID 12884281HCID 12884281, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 0.4 parts of N,N-dicyclohexylcarbodiimide in 5 parts of dioxane was added at once to a solution of 0.6 parts of 2-(4-chloro-2-fluorophenylaminocarbonyl)-1-cyclohexene-1-carboxylic acid in 5 parts of dioxane to form a slurry. After stirring the slurry for 1 hour, the resulting solid 1,3-dicyclohexylurea was filtered. The filtrate was evaporated under reduced pressure of 300 mm. Hg at 25° C to a yellow, semisolid residue from which 0.27 parts of 3-(4-chloro-2-fluorophenylimino)-4,5,6,7-tetrahydro-1-(3H)-isobenzofuranone melting at 81°-84° C was isolated after fractionation by high pressure liquid chromatography.

Workup

  1. customto form a slurry
  2. filtrationthe resulting solid 1,3-dicyclohexylurea was filtered
  3. customThe filtrate was evaporated under reduced pressure of 300 mm. Hg at 25° C to a yellow, semisolid residue from which 0.27 parts of 3-(4-chloro-2-fluorophenylimino)-4,5,6,7-tetrahydro-1-(3H)-isobenzofuranone melting at 81°-84° C
  4. customwas isolated after fractionation by high pressure liquid chromatography

Sources & evidence

ORD record
ord-bf9f4f2ea4404c9e8b1370b114dddb0c
Source dataset
uspto-grants-1976_11
Patent number
US03990880

Reaction notes

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