N,N-Diethylaniline → Propan-2-yl (3-chloro-4-ethoxy-5-ethylphenyl)carbamate

HRID 2308732Notes

Reaction equation

HRID 2308732 reaction equation
[CH2:1]([C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([Cl:13])[C:9]=1[O:10][CH2:11][CH3:12])[NH2:6])[CH3:2].CCN(C1C=CC=CC=1)CC.Cl[C:26]([O:28][CH:29]([CH3:31])[CH3:30])=[O:27]>C1(C)C=CC=CC=1>[CH2:1]([C:3]1[CH:4]=[C:5]([NH:6][C:26](=[O:27])[O:28][CH:29]([CH3:31])[CH3:30])[CH:7]=[C:8]([Cl:13])[C:9]=1[O:10][CH2:11][CH3:12])[CH3:2]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 201875993-Chloro-4-ethoxy-5-ethylbenzenamine

Product 1

HCID 13303908Propan-2-yl (3-chloro-4-ethoxy-5-ethylphenyl)carbamateYield 89%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Ethyl-4-ethoxy-5-chloroaniline (1.9 g) and diethylaniline (1.5 g) were dissolved in toluene (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 temperature for 12 hours, the reaction mixture was poured into ice-water and extracted with toluene. The extract was washed with water, dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography using toluene as the eluent to give isopropyl N-(3-ethyl-4-ethoxy-5-chlorophenyl)carbamate (Compound No. 53) (2.4 g) in a yield of 89%. M.P., 79°-80.5° C.

Workup

  1. customin 5 minutes
  2. temperaturecooling
  3. extractionextracted with toluene
  4. washThe extract was washed with water
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-5ebd424459dc4d049d4a43624337c9d3
Source dataset
uspto-grants-1987_09
Patent number
US04690946

Reaction notes

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