Diphosgene → HCID 14053649, compound

HRID 1762275Notes

Reaction equation

HRID 1762275 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[N:11]1[C:19](=O)[C:18]2[CH2:17][CH2:16][CH2:15][CH2:14][C:13]=2[NH:12]1.[Cl:21]C(OC(Cl)(Cl)Cl)=O>C1(C)C=CC=CC=1.ClCCCl>[Cl:21][C:19]1[N:11]([C:3]2[CH:4]=[C:5]([N+:8]([O-:10])=[O:9])[CH:6]=[CH:7][C:2]=2[F:1])[N:12]=[C:13]2[C:18]=1[CH2:17][CH2:16][CH2:15][CH2:14]2

Participants

5

Reactant 2

HCID 10426DiphosgeneHCID 14053650HCID 14053650, compound

Product 1

HCID 14053649HCID 14053649, compound

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolvent

Procedure

To a solution of 2-(2-fluoro-5-nitrophenyl)-1,2,4,5,6,7-hexahydro-3H-indazol-3-one (66.87 g) in toluene (125 ml) and 1,2-dichloroethane (175 ml), there was added trichloromethyl chloroformate (71.57 g), and the resultant mixture was allowed to react in an autoclave at a temperature of 120° to 130° C. under a pressure of 25 kg/cm2 for 3 hours. After cooling, the solvent was removed by distillation. The residue was purified by silica gel column chromatography using a mixture of ethyl acetate and n-hexane (1:6) as an eluent to give 3chloro-2-(2-fluoro-5-nitrophenyl)-4,5,6,7-tetrahydro-2H-indazole. m.p. 109.1° C.

Workup

  1. customto react in an autoclave at a temperature of 120° to 130° C. under a pressure of 25 kg/cm2 for 3 hours
  2. temperatureAfter cooling
  3. customthe solvent was removed by distillation
  4. customThe residue was purified by silica gel column chromatography
  5. additiona mixture of ethyl acetate and n-hexane (1:6) as an eluent

Sources & evidence

ORD record
ord-be96a15eb47d4898bb574d66b81834ff
Source dataset
uspto-grants-1989_05
Patent number
US04831150

Reaction notes

Loading…