N,N-Diethylaniline → HCID 13150467, compound

HRID 615882Notes

Reaction equation

HRID 615882 reaction equation
[CH:1]([O:4][C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([O:12][CH:13]([CH3:15])[CH3:14])[CH:11]=1)[NH2:8])([CH3:3])[CH3:2].CCN(C1C=CC=CC=1)CC.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>C1C=CC=CC=1>[CH:13]([O:12][C:10]1[CH:9]=[C:7]([NH:8][C:28](=[O:29])[O:30][CH2:31][CH3:32])[CH:6]=[C:5]([O:4][CH:1]([CH3:3])[CH3:2])[CH:11]=1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 10928Ethyl chloroformateHCID 134578593,5-Bis[(propan-2-yl)oxy]aniline

Product 1

HCID 13150467HCID 13150467, compoundYield 70.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,5-Diisopropyloxyaniline (2 g) and diethylaniline (1.5 g) were dissolved in benzene (20 ml). To the resultant mixture was dropwise added ethyl chloroformate (1.2 g) under ice-cooling. After being allowed to stand at room temperature for 12 hours, the reaction mixture was poured into ice water and extracted with ethyl acetate. The extract was washed with water, dried over magnesium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel chromatography using a mixture of benzene and tetrahydrofuran as the eluent to give ethyl N-(3,5-diisopropyloxyphenyl)carbamate (1.9 g) in a yield of 67.6%. M.P., 81.5°-82° C.

Workup

  1. temperaturecooling
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over magnesium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was purified by silica gel chromatography
  7. additiona mixture of benzene and tetrahydrofuran as the eluent

Sources & evidence

ORD record
ord-189654e5bbb54e148746d2f79d42d8a7
Source dataset
uspto-grants-1985_02
Patent number
US04501756

Reaction notes

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