Diphosgene → HCID 13881569, compound

HRID 477434Notes

Reaction equation

HRID 477434 reaction equation
[F:1][C:2]1([F:13])[CH2:4][CH:3]1[O:5][C:6]1[CH:12]=[CH:11][C:9]([NH2:10])=[CH:8][CH:7]=1.Cl[C:15](OC(Cl)(Cl)Cl)=[O:16].[Cl:22][C:23]1[CH:28]=[CH:27][C:26]([C:29]2[CH:33]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[CH2:32][NH:31][N:30]=2)=[CH:25][CH:24]=1>O1CCOCC1.ClCCl>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([C:29]2[CH:33]([C:34]3[CH:39]=[CH:38][C:37]([Cl:40])=[CH:36][CH:35]=3)[CH2:32][N:31]([C:15]([NH:10][C:9]3[CH:11]=[CH:12][C:6]([O:5][CH:3]4[CH2:4][C:2]4([F:13])[F:1])=[CH:7][CH:8]=3)=[O:16])[N:30]=2)=[CH:27][CH:28]=1

Participants

6

Reactant 3

HCID 10426DiphosgeneHCID 13726940HCID 13726940, compoundHCID 13881568HCID 13881568, compound

Product 1

HCID 13881569HCID 13881569, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

4-(2,2-Difluorocyclopropyloxy)aniline was dissolved in dioxane (10 ml) and treated with tricloromethyl chloroformate (0.6 ml). The mixture was heated at 100° C. for 3 hours whilst excluding moisture. The mixture was then cooled to room temperature and 3,4-bis-(4-chlorophenyl)-4,5-dihydropyrazole (2.64 g; 9 mmol), dissolved in dichloromethane (30 ml), was added with stirring. After 3 hours the reaction mixture was concentrated and the residue chromatographed on silica gel.

Workup

  1. temperatureThe mixture was then cooled to room temperature
  2. additionwas added
  3. concentrationAfter 3 hours the reaction mixture was concentrated
  4. customthe residue chromatographed on silica gel

Sources & evidence

ORD record
ord-d3dd4a35a97c4ecea3c7455c117f4e31
Source dataset
uspto-grants-1989_12
Patent number
US04888340

Reaction notes

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