Water → HCID 13961081, compound

HRID 2309319Notes

Reaction equation

HRID 2309319 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[CH:6][C:5]([NH:12][NH2:13])=[C:4]([F:14])[CH:3]=1.C1(C)C=CC=CC=1.C([O:24][C:25]([CH:27]1[CH2:32][CH2:31][CH2:30][CH2:29][C:28]1=O)=O)C.O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH:9]([F:11])[F:10])=[CH:6][C:5]([N:12]2[C:25](=[O:24])[C:27]3[CH2:32][CH2:31][CH2:30][CH2:29][C:28]=3[NH:13]2)=[C:4]([F:14])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 1140TolueneHCID 95543Ethyl 2-oxocyclohexanecarboxylateHCID 184768(4-Chloro-5-(difluoromethoxy)-2-fluorophenyl)hydrazine

Product 1

HCID 13961081HCID 13961081, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To 12.7 g of 4-chloro-5-difluoromethoxy-2-fluorophenylhydrazine were added 127 ml of toluene and 9.5 g of 2-ethoxycarbonylcyclohexanone V-1, and the resultant mixture was refluxed for 24 hours. After cooling, the reaction mixture was mixed with water and shaken with chloroform. The chloroform layer was dried and concentrated. The residue was chromatographed on a column of silica gel, eluting with n-hexane-ethyl acetate (1:1 v/v). The elutate was concentrated to give 6,0 g of the titled compound VIII-1 (containing a certain amount of its tautomer 2,3a,4,5,6,7-hexahydro compound).

Workup

  1. temperatureAfter cooling
  2. dry with materialThe chloroform layer was dried
  3. concentrationconcentrated
  4. customThe residue was chromatographed on a column of silica gel
  5. washeluting with n-hexane-ethyl acetate (1:1 v/v)
  6. concentrationThe elutate was concentrated

Sources & evidence

ORD record
ord-d5bb089f37094eea8807cfef86af3e28
Source dataset
uspto-grants-1987_09
Patent number
US04695312

Reaction notes

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