Hydrochloric Acid → HCID 86734494, compound

HRID 839302Notes

Reaction equation

ClC1C=CC([N:8]([C:10](=O)[C:11]([CH3:14])([CH3:13])[CH3:12])[NH2:9])=CC=1.P(Cl)(Cl)(Cl)(Cl)[Cl:17].[ClH:22].[C:23]1(O)[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>C(Cl)(Cl)(Cl)Cl>[Cl:22][C:26]1[CH:27]=[CH:28][C:23]([NH:9][N:8]=[C:10]([Cl:17])[C:11]([CH3:14])([CH3:13])[CH3:12])=[CH:24][CH:25]=1

Participants

Conditions

Temperature: 5 °C

Procedure

A quantity (15.9 g.; 0.07 mole) of pivalic acid (4-chlorophenyl)hydrazide prepared in Part A, above, and 15.3 g. (0.0735 mole) of phosphorous pentachloride were stirred together in 100 ml. of carbon tetrachloride. The suspension was heated at the reflux temperature for 15 min., when the evolution of hydrogen chloride ceased. The reaction mixture was cooled to about 5° C. and 22.2 g. (0.236 mole) of phenol was added. After the evolution of hydrogen chloride had ceased the carbon tetrachloride was removed by evaporation under reduced pressure and the residual oil was chromatographed on 1 kg. of silica gel. Elution of the column with equal parts of benzene and technical hexane and evaporation of the solvent mixture from the eluate gave pivaloyl chloride (4-chlorophenyl)hydrazone which was recrystallized from petroleum ether. The product thus obtained had a melting point of 42° to 43° C.

Workup

temperatureThe suspension was heated at the reflux temperature for 15 min.
customwas removed by evaporation under reduced pressure
customthe residual oil was chromatographed on 1 kg
washElution of the column
customwith equal parts of benzene and technical hexane and evaporation of the solvent mixture from the

Sources & evidence

ORD record: ord-1c02a666330d498d8e993b97f33c92b1
Source dataset: uspto-grants-1978_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04094906

Reaction notes

Loading…