N,N-Diethylaniline → HCID 13326690, compound

HRID 1905762Notes

Reaction equation

HRID 1905762 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([CH2:14][O:15][CH3:16])[C:8]=1[O:9][C:10](=[O:13])[NH:11][CH3:12])[NH2:5].C(N(CC)C1C=CC=CC=1)C.Cl[C:29]([O:31][CH:32]([CH3:34])[CH3:33])=[O:30]>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:29](=[O:30])[O:31][CH:32]([CH3:34])[CH3:33])[CH:6]=[C:7]([CH2:14][O:15][CH3:16])[C:8]=1[O:9][C:10](=[O:13])[NH:11][CH3:12]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 13326689HCID 13326689, compound

Product 1

HCID 13326690HCID 13326690, compoundYield 90.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

3-Chloro-4-methylcarbamoyloxy-5-methoxymethylaniline (1.0 g) and N,N-diethylaniline (0.90 g) were dissolved in toluene (15 ml). To the resultant solution was dropwise added isopropyl chloroformate (0.75 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 benzene and tetrahydrofuran as the eluent to give isopropyl N-(3-chloro-4-methylcarbamoyloxy-5-methoxymethylphenyl)carbamate (Compound No. 4) (1.22 g) in a yield of 90.5%. M.P., 113°-114° 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-c2a1fb5f35304f06aef15d77ac08c9e1
Source dataset
uspto-grants-1987_03
Patent number
US04647584

Reaction notes

Loading…