Phosgene → HCID 20134769, compound

HRID 580314Notes

Reaction equation

HRID 580314 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:17](OCC)(=[O:19])C.C(Cl)(Cl)=O>C1(C)C=CC=CC=1>[CH2:1]([O:3][C:4]1[C:9]([Cl:10])=[CH:8][C:7]([N:11]=[C:17]=[O:19])=[CH:6][C:5]=1[NH:12][C:13](=[O:16])[O:14][CH3:15])[CH3:2]

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 8857Ethyl AcetateHCID 13421317HCID 13421317, compound

Product 1

HCID 20134769HCID 20134769, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Methyl N-(2-ethoxy-3-chloro-5-aminophenyl)carbamate (2.67 g) in toluene (20 ml) was dropwise added to an ethyl acetate solution containing 10 g of phosgene at 10° to 20° C. The resultant mixture was gradually heated and, after being refluxed for 30 minutes, cooled to room temperature. The solvent was removed by distillation under reduced pressure to give methyl N-(2-ethoxy-3-chloro-5-isocyanatophenyl)carbamate. The thus obtained crude substance was added to a toluene solution (50 ml) containing triethylamine (1.0 g) and 3-buten-2-ol (0.79 g). 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 1-methyl-2-propenyl N-(3-chloro-4-ethoxy-5-methoxycarbonylaminophenyl)carbamate (Compound No. 3) (3.57 g) in a yield of 95.6 %. nD25.0 1.5383.

Workup

  1. temperatureafter being refluxed for 30 minutes
  2. customThe solvent was removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-5abed63f4d424ae096f9d9eda0aec273
Source dataset
uspto-grants-1988_06
Patent number
US04752615

Reaction notes

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