Chloroform → HCID 19852517, compound

HRID 1607233Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(C)([O-])C.[K+].[CH:26]([Cl:29])(Cl)[Cl:27].[F:30][C:31]([F:58])([F:57])[O:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([N:42]2[CH2:46][C:45]([CH:48]=O)([CH3:47])[C:44]([C:50]3[CH:55]=[CH:54][C:53]([Cl:56])=[CH:52][CH:51]=3)=[N:43]2)=[O:41])=[CH:35][CH:34]=1>C1COCC1>[F:58][C:31]([F:30])([F:57])[O:32][C:33]1[CH:38]=[CH:37][C:36]([NH:39][C:40]([N:42]2[CH2:46][C:45]([CH:47]=[C:26]([Cl:29])[Cl:27])([CH3:48])[C:44]([C:50]3[CH:51]=[CH:52][C:53]([Cl:56])=[CH:54][CH:55]=3)=[N:43]2)=[O:41])=[CH:35][CH:34]=1

Participants

Conditions

Temperature: -70 °C

Procedure

To 6.5 g of triphenyl phosphine and 2.5 g of potassium t-butoxide dissolved in 75 ml of THF and cooled to -70° C. was added 3.5 g of chloroform. After stiring for 5 minutes a solution of 3.9 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-formyl-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide in 10 ml of THF is added and the mixture is allowed to warm to 10° C. over 1 hour. The resulting mixture is partitioned between ether and water, dried, rotovaped and chromatographed (ether/hexane) on silica gel yielding 3.1 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-(2,2-dichlorovinyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide mp 138°-141° C. NMR and IR data were consistent with the structure.

Workup

temperatureto warm to 10° C. over 1 hour
customThe resulting mixture is partitioned between ether and water
customdried
customchromatographed (ether/hexane) on silica gel yielding 3.1 g of N-(4-trifluoromethoxyphenyl)-3-(4-chlorophenyl)-4-(2,2-dichlorovinyl)-4-methyl-4,5-dihydro-1H-pyrazole-1-carboxamide mp 138°-141° C

Sources & evidence

ORD record: ord-fe55566506884cbdb4028f65db7320e3
Source dataset: uspto-grants-1989_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04863947

Reaction notes

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