Benzoyl chloride → isopropyl N-benzoyl-N-(3,4-diethoxyphenyl)carbamate

HRID 365118Notes

Reaction equation

[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:13][C:14](=[O:19])[O:15][CH:16]([CH3:18])[CH3:17])[CH:7]=[CH:8][C:9]=1[O:10][CH2:11][CH3:12])[CH3:2].[H-].[Na+].[C:22](Cl)(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C)C=O>[C:22]([N:13]([C:6]1[CH:7]=[CH:8][C:9]([O:10][CH2:11][CH3:12])=[C:4]([O:3][CH2:1][CH3:2])[CH:5]=1)[C:14](=[O:19])[O:15][CH:16]([CH3:17])[CH3:18])(=[O:29])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Isopropyl N-(3,4-diethoxyphenyl)carbamate (2.7 g) was dissolved in dimethylformamide (50 ml), and sodium hydride dispersion (50%, 0.5 g) was added thereto. The mixture was heated at 60° C. for 15 minutes, treated with benzoyl chloride (1.4 g) and heated for 30 minutes. The reaction mixture was poured into ice-water and extracted with ether. The extract was washed with sodium bicarbonate solution and saturated brine, dried over anhydrous magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using hexane-acetone as the eluent to give isopropyl N-benzoyl-N-(3,4-diethoxyphenyl)carbamate (Compound No. 99) (3.1 g) in a yield of 80%. M.P., 120°-121° C.

Workup

temperatureheated for 30 minutes
extractionextracted with ether
washThe extract was washed with sodium bicarbonate solution and saturated brine
dry with materialdried over anhydrous magnesium sulfate
concentrationconcentrated under reduced pressure
customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record: ord-8a3989a0c0824897817a60bab13e9bde
Source dataset: uspto-grants-1986_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04608385

Reaction notes

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