Triethylamine → HCID 14835675, compound

HRID 1709242Notes

Reaction equation

[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](O)=[O:8].C(N(CC)CC)C.C(Cl)(=O)OCC.O.[NH2:29][NH2:30]>C(Cl)Cl>[CH3:1][O:2][CH:3]([O:13][CH3:14])[C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7]([NH:29][NH2:30])=[O:8]

Participants

Conditions

Temperature: -55 °C

Procedure

3.92 g of 3-dimethoxymethylbenzoic acid and 2.22 g of triethylamine were dissolved in 40 ml of methylene chloride. To the solution was dropwise added 2.28 g of ethyl chlorocarbonate at -30° to -20° C. The mixture was stirred for 30 minutes at the same temperature. The mixture was then cooled to -55° C., and 5.00 g of hydrazine hydrate was added thereto. The temperature of the mixture was elevated to room temperature. The methylene chloride layer was separated, washed with water and a saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate. The solvent was removed by distillation under reduced pressure. The residue was purified by a column chromatography (eluant: chloroform/ethanol=30/1) to obtain 4.13 g of colorless oily 3-dimethoxymethylbenzhydrazide.

Workup

customat -30° to -20° C
customwas elevated to room temperature
customThe methylene chloride layer was separated
washwashed with water
dry with materiala saturated aqueous sodium chloride solution in this order and dried over anhydrous magnesium sulfate
customThe solvent was removed by distillation under reduced pressure
customThe residue was purified by a column chromatography (eluant: chloroform/ethanol=30/1)

Sources & evidence

ORD record: ord-18ef36b78ea44a8d85845e99928a62e3
Source dataset: uspto-grants-1990_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04948796

Reaction notes

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