N,N-Diethylaniline → Diethofencarb

HRID 365116Notes

Reaction equation

HRID 365116 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH3:13])[NH2:7])[CH3:2].CCN(C1C=CC=CC=1)CC.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C1C=CC=CC=1>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([NH:7][C:26](=[O:27])[O:28][CH:29]([CH3:31])[CH3:30])[CH:8]=[CH:9][C:10]=1[O:11][CH2:12][CH3:13])[CH3:2]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 5209363,4-Diethoxyaniline

Product 1

HCID 91742DiethofencarbYield 87.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,4-Diethoxyaniline (1.8 g) and diethylaniline (1.5 g) were dissolved in benzene (20 ml). To the resultant solution was dropwise added isopropyl chloroformate (1.2 g) in 5 minutes under ice-cooling. After being allowed to stand at room temperatue for 3 hours, the reaction mixture was poured into ice-water and extracted with ether. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure to give crude crystals (2.6 g). Recrystallization from ethanol gave isopropyl N-(3,4-diethoxyphenyl)carbamate (Compound No. 13) (2.3 g) in a yield of 86%. M.P., 100°-100.5° C.

Workup

  1. customin 5 minutes
  2. temperaturecooling
  3. extractionextracted with ether
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give crude crystals (2.6 g)
  8. customRecrystallization from ethanol

Sources & evidence

ORD record
ord-21b2ed92a9c344b5ad2bf0dabadc72d1
Source dataset
uspto-grants-1986_08
Patent number
US04608385

Reaction notes

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