Acetic Acid → HCID 19770728, compound

HRID 1681112Notes

Reaction equation

[CH2:1]([O:8][CH2:9][C:10](Cl)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:18][CH3:19])CC)C.[NH4+].[N+:21]([CH2:24][C:25]([NH-:27])=[O:26])([O-:23])=[O:22].[C:28](O)(=O)[CH3:29]>O1CCCC1.C(Cl)(Cl)Cl>[N+:21]([C:24]1[C:25](=[O:26])[NH:27][C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:28]([CH2:18][CH3:19])[CH:29]=1)([O-:23])=[O:22]

Participants

Conditions

Temperature: 70 °C

Procedure

Benzyloxyacetylchloride (14.2 mL, 0.09 mol) in dry tetrahydrofuran (10 mL) was added dropwise to a solution of 1-(N-morpholino)-1-butene (12.8 g, 0.09 mol) and triethylamine (12.6 mL, 0.09 mol) in dry tetrahydrofuran (120 mL) warmed at 70° C. under a nitrogen atmosphere. After 1.25 hours, the reaction was cooled to room temperature and nitroacetamide ammonium salt (12.0 g, 0.099 mol) was added followed by the dropwise addition of acetic acid (11.4 mL, 0.20 mol). After stirring for 20-24 hours, the reaction was diluted with chloroform (150 mL) and the solution washed with water, 10% HCl, dried (Na2SO4) and filtered througha pad of charcoal. The solvent was removed and the residue triturated with cold methanol. The crystalline yellow product was filtered, rinsed with methanol and diethyl ether to give the title compound, mp 157°-158° C.

Workup

temperaturethe reaction was cooled to room temperature
washthe solution washed with water, 10% HCl
dry with materialdried (Na2SO4)
filtrationfiltered througha pad of charcoal
customThe solvent was removed
customthe residue triturated with cold methanol
filtrationThe crystalline yellow product was filtered
washrinsed with methanol and diethyl ether

Sources & evidence

ORD record: ord-61ab6fceb73643a09365363d6a9d809a
Source dataset: uspto-grants-1992_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05169769

Reaction notes

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