N,N-Diethylaniline → Carbamic acid, (3,4-diethoxy-2-fluorophenyl)-, 1-methylethyl ester

HRID 364645Notes

Reaction equation

HRID 364645 reaction equation
[F:1][C:2]1[C:8]([O:9][CH2:10][CH3:11])=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=[CH:5][C:3]=1[NH2:4].C(N(CC)C1C=CC=CC=1)C.Cl[C:27]([O:29][CH:30]([CH3:32])[CH3:31])=[O:28]>C1(C)C=CC=CC=1>[F:1][C:2]1[C:8]([O:9][CH2:10][CH3:11])=[C:7]([O:12][CH2:13][CH3:14])[CH:6]=[CH:5][C:3]=1[NH:4][C:27](=[O:28])[O:29][CH:30]([CH3:32])[CH3:31]

Participants

5

Reactant 3

HCID 7061N,N-DiethylanilineHCID 7917Isopropyl chloroformateHCID 134544923,4-Diethoxy-2-fluoroaniline

Product 1

HCID 13454493Carbamic acid, (3,4-diethoxy-2-fluorophenyl)-, 1-methylethyl esterYield 94.5%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

2-Fluoro-3,4-diethoxyaniline (0.17 g) and N,N-diethylaniline (0.13 g) were dissolved in toluene (15 ml). To the resultant solution was dropwise added isopropyl chloroformate (0.11 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-(2-fluoro-3,4-diethoxyphenyl)carbamate (Compound No. 1) (0.23 g) in a yield of 94.4%. M.P., 79°-81° 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 toluene and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-9820ab081de64f23b54590825c7b3618
Source dataset
uspto-grants-1986_08
Patent number
US04605668

Reaction notes

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