Phosphorus oxychloride → 3-Chloro-2-(4-chlorophenyl)-2,4,5,6,7,8-hexahydrocycloheptapyrazole

HRID 2419973Notes

Reaction equation

HRID 2419973 reaction equation
Cl.[Cl:2]C1C=CC(NN)=CC=1.[Cl:11][C:12]1[CH:17]=[CH:16][C:15]([N:18]2[C:22](=O)[C:21]3[CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][C:20]=3[NH:19]2)=[CH:14][CH:13]=1.N1C=CC(=O)N=1.P(Cl)(Cl)(Cl)=O>>[Cl:2][C:22]1[N:18]([C:15]2[CH:16]=[CH:17][C:12]([Cl:11])=[CH:13][CH:14]=2)[N:19]=[C:20]2[CH2:28][CH2:27][CH2:26][CH2:25][CH2:24][C:21]=12

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 71600Hydrazine, (4-chlorophenyl)-, hydrochloride (1:1)HCID 11513733PyrazoloneHCID 203121642-(4-chlorophenyl)-1,4,5,6,7,8-hexahydrocycloheptapyrazol-3(2H)-one

Product 1

HCID 203121633-Chloro-2-(4-chlorophenyl)-2,4,5,6,7,8-hexahydrocycloheptapyrazole

Procedure

By substituting 2-carbethoxycycloheptanone [prepared by the method of G. Stork, et al., J. Am. Chem. Soc., 85, 207 (1963)] and p-chlorophenylhydrazine hydrochloride (available from Aldrich Chemical Company) in the procedure of Example 1(c), 2-(4-chlorophenyl)-1,4,5,6,7,8-hexahydrocycloheptapyrazol-3(2H)-one (m.p. 224°-225°) was prepared. By reacting this pyrazolone with phosphorous oxychloride according to the procedure of Example 1(d), 3-chloro-2-(4-chlorophenyl)-2,4,5,6,7,8-hexahydrocycloheptapyrazole (m.p. 59°-61°) was obtained.

Workup

  1. customprepared by the method of G

Sources & evidence

ORD record
ord-25604fa430e84e15801d92411e7418dc
Source dataset
uspto-grants-1978_08
Patent number
US04108628

Reaction notes

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