N,N-Diethylaniline → HCID 13388244, compound

HRID 580313Notes

Reaction equation

HRID 580313 reaction equation
[CH2:1]([O:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([NH2:11])=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[O:14][CH3:15])[CH3:2].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:10][C:9]1[CH:8]=[C:7]([NH:11][C:29](=[O:30])[O:31][CH:32]([CH3:34])[CH3:33])[CH:6]=[C:5]([NH:12][C:13]([O:14][CH3:15])=[O:16])[C:4]=1[O:3][CH2:1][CH3:2]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 13421317HCID 13421317, compound

Product 1

HCID 13388244HCID 13388244, compoundYield 92.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl N-(2-ethoxy-3-chloro-5-aminophenyl)carbamate (1.39 g) and N,N-diethylaniline (0.85 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 toluene and ethyl acetate as the eluent to give isopropyl N-(3-chloro-4-ethoxy-5-methoxycarbonylaminophenyl)carbamate (Compound No. 2) (1.73 g) in a yield of 92.0%. M.P., 140° C.-142° 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 toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-12b096350a50486caeea6946477b4158
Source dataset
uspto-grants-1988_06
Patent number
US04752615

Reaction notes

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