Phosgene → Methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate

HRID 703045

반응식

HRID 703045 반응식
[NH2:1][S:2]([C:5]1[CH:14]=[C:13]([O:15][CH2:16][CH3:17])[CH:12]=[CH:11][C:6]=1[C:7]([O:9][CH3:10])=[O:8])(=[O:4])=[O:3].C(N=[C:23]=[O:24])CCC.C(Cl)(Cl)=O>>[CH2:16]([O:15][C:13]1[CH:12]=[CH:11][C:6]([C:7]([O:9][CH3:10])=[O:8])=[C:5]([S:2]([N:1]=[C:23]=[O:24])(=[O:3])=[O:4])[CH:14]=1)[CH3:17]

참가 물질

4

반응물 3

HCID 6371PhosgeneHCID 8110Butyl isocyanateHCID 13987872Methyl 2-(aminosulfonyl)-4-ethoxybenzoate

생성물 1

HCID 13987873Methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate수율 98.4%

실험 절차

A solution of methyl 2-(aminosulfonyl)-4-ethoxybenzoate (7.56 g. 29.2 mmol). n-butyl isocyanate (3.29 mL. 29.2 mmol). and 1.4-diaza[2.2.2]bicyclooctane (0.13 g 1.2 mmol) in mixed xylenes was heated at reflux for 10 minutes. Phosgene was then added at such a rate that the internal temperature stayed at 133° C. or above. When consumption of phosgene ceased, the solution was cooled to room temperature and then filtered under nitrogen. Rotary evaporation gave methyl 4-ethoxy-2-(isocyanatosulfonyl)benzoate as a cloudy yellow oil (8.2 g). This was used immediately without further purification or characterization.

후처리

  1. temperatureat reflux for 10 minutes
  2. customstayed at 133° C. or above
  3. customWhen consumption of phosgene
  4. filtrationfiltered under nitrogen
  5. customRotary evaporation

출처 및 근거

ORD 기록
ord-395aae7db70c45e1850be94acd1d7640
출처 데이터셋
uspto-grants-1991_01
특허 번호
US04981509

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