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

HRID 365118
Notes
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Reaction equation

HRID 365118 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 24758Sodium hydrideHCID 91742Diethofencarb

Product 1

HCID 13421255isopropyl N-benzoyl-N-(3,4-diethoxyphenyl)carbamateYield 80%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

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

  1. temperatureheated for 30 minutes
  2. extractionextracted with ether
  3. washThe extract was washed with sodium bicarbonate solution and saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes