N,N-Diethylaniline → HCID 13339703, compound

HRID 1905708Notes

Reaction equation

HRID 1905708 reaction equation
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:9]=[C:10]([O:15][CH2:16][CH3:17])[C:11]=1[O:12][CH2:13][CH3:14])[NH2:8])(=[O:3])[CH3:2].C(N(CC)C1C=CC=CC=1)C.Cl[C:30]([O:32][CH:33]([CH3:35])[CH3:34])=[O:31]>C1(C)C=CC=CC=1>[C:1]([O:4][C:5]1[CH:6]=[C:7]([NH:8][C:30](=[O:31])[O:32][CH:33]([CH3:35])[CH3:34])[CH:9]=[C:10]([O:15][CH2:16][CH3:17])[C:11]=1[O:12][CH2:13][CH3:14])(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 20215179HCID 20215179, compound

Product 1

HCID 13339703HCID 13339703, compoundYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Acetyloxy-4,5-diethoxyaniline (1.0 g) and N,N-diethylaniline (0.70 g) were dissolved in toluene (15 ml). To the resultant solution was dropwise added isopropyl chloroformate (0.70 g) in 5 minutes under ice-cooling. The resultant mixture was allowed to stand at room temperature for 12 hours, 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 reside was purified by silica gel chromatography using a mixture of benzene and tetrahydrofuran as the eluent to give isopropyl N-(3-acetyloxy-4,5-diethoxyphenyl)carbamate (Compound No. 4) (1.21 g) in a yield of 88.9%. M.P., 108°-109° C.

Workup

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

Sources & evidence

ORD record
ord-18c0d9c565404db3bd7204640174d447
Source dataset
uspto-grants-1987_03
Patent number
US04647582

Reaction notes

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