N,N-Diethylaniline → HCID 13422317, compound

HRID 979233Notes

Reaction equation

HRID 979233 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:12])[C:8]=1[CH2:9][O:10][CH3:11])[NH2:5].C(N(CC)C1C=CC=CC=1)C.Cl[C:25]([O:27][CH:28]([CH3:30])[CH3:29])=[O:26]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:25](=[O:26])[O:27][CH:28]([CH3:30])[CH3:29])[CH:6]=[C:7]([Cl:12])[C:8]=1[CH2:9][O:10][CH3:11]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 20201866HCID 20201866, compound

Product 1

HCID 13422317HCID 13422317, compoundYield 89.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3,5-Dichloro-4-methoxymethylaniline (2.06 g) and N,N-diethylaniline (1.49 g) were dissolved in toluene (15 ml). To the resultant solution was dropwise added isopropyl chloroformate (1.24 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 residue was purified by silica gel chromatography using a mixture of toluene and ethyl acetate as the eluent to give isopropyl N-(3,5-dichloro-4-methoxymethylphenyl)carbamate (Compound No. 1) (2.62 g) in a yield of 89.6% nD26.2 1.5283.

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 residue was purified by silica gel chromatography
  8. additiona mixture of toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-1a3b380f4ea34bd6ba5303e0da040747
Source dataset
uspto-grants-1987_05
Patent number
US04666938

Reaction notes

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