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

HRID 231738

反応式

HRID 231738 の反応式
[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]

参加物

4

反応物 3

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

生成物 1

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

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-88907d0077da42188bd8d824f5eca525
出典データセット
uspto-grants-1989_07
特許番号
US04849010

関連ノート

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