Toluene → (S)-N'-(2-(Benzyloxy)propylidene)formohydrazide

HRID 512813Notes

Reaction equation

[CH:1]([NH:3][NH2:4])=[O:2].C1(C)C=CC=CC=1.[CH2:12]([O:19][C@@H:20]([CH3:23])[CH:21]=O)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CO>[CH2:12]([O:19][C@@H:20]([CH3:23])[CH:21]=[N:4][NH:3][CH:1]=[O:2])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 27.5 °C

Procedure

To a pre-cooled solution of formyl hydrazine (40.3 g) in methanol (290 ml) at 0-5° C., toluene layer containing (S)-2-(benzyloxy)propanal compound of formula-15 obtained in step-b) was added. Slowly raised the temperature of reaction mixture to 25-30° C. and stirred for 4 hours at 25-30° C. After completion of the reaction, distilled off the solvent under reduced pressure to get title compound. Ethyl acetate (210 ml) was added to the obtained compound and stirred for 1 hour at 25-30° C. Filtered the reaction mixture to remove the unwanted solid and washed with ethyl acetate. Distilled off the solvent completely from the filtrate under reduced pressure to get semi-solid. Petroleum ether (210 ml) was added to the obtained semi-solid and stirred for 2 hours at 25-30° C. Filtered the precipitated solid, washed with petroleum ether and then dried to get title compound.

Workup

customobtained in step-b)
additionwas added
temperatureSlowly raised
customthe temperature of reaction mixture to 25-30° C.
customAfter completion of the reaction
distillationdistilled off the solvent under reduced pressure

Sources & evidence

ORD record: ord-551826d5a9bc45b5bb909f5af6340cba
Source dataset: uspto-grants-2015_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09102664B2

Reaction notes

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