N,N-Diethylaniline → Propan-2-yl (3,5-dichloro-4-methoxyphenyl)carbamate

HRID 2308730Notes

Reaction equation

HRID 2308730 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:11])[C:8]=1[O:9][CH3:10])[NH2:5].CCN(C1C=CC=CC=1)CC.Cl[C:24]([O:26][CH:27]([CH3:29])[CH3:28])=[O:25]>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:24](=[O:25])[O:26][CH:27]([CH3:29])[CH3:28])[CH:6]=[C:7]([Cl:11])[C:8]=1[O:9][CH3:10]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 131786513,5-Dichloro-4-methoxyaniline

Product 1

HCID 13178652Propan-2-yl (3,5-dichloro-4-methoxyphenyl)carbamateYield 92.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

3,5-Dichloro-4-methoxyaniline (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 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 isopropyl N-(3,5-dichloro-4-methoxyphenyl)carbamate (Compound No. 2) (2.4 g) in a yield of 91.8%. M.P., 107.5°-108° 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 residue was purified by silica gel chromatography
  8. additiona mixture of benzene and tetrahydrofuran as the eluent

Sources & evidence

ORD record
ord-09f81c9d9d5d4359a2be46c6df4250df
Source dataset
uspto-grants-1987_09
Patent number
US04690946

Reaction notes

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