Triethylamine → 4-(Butylsulfamoyl)phenyl 2-methylprop-2-enoate

HRID 1156418ノート

反応式

HRID 1156418 の反応式
[C:1](Cl)(=[O:5])[C:2]([CH3:4])=[CH2:3].[CH2:7]([NH:11][S:12]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)(=[O:14])=[O:13])[CH2:8][CH2:9][CH3:10].C(N(CC)CC)C>C(Cl)Cl>[CH2:7]([NH:11][S:12]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:1](=[O:5])[C:2]([CH3:4])=[CH2:3])=[CH:19][CH:20]=1)(=[O:14])=[O:13])[CH2:8][CH2:9][CH3:10]

参加物

5

反応物 3

HCID 8471TriethylamineHCID 13528Methacryloyl chlorideHCID 11736345N-Butyl-4-hydroxybenzenesulfonamide

生成物 1

HCID 205361454-(Butylsulfamoyl)phenyl 2-methylprop-2-enoate収率 65.4%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

A solution of 20.91 g (0.20 mol) of methacryloyl chloride in 80 ml of methylene chloride was added to a solution of 45.86 g (0.20 mol) of N-butyl-4-hydroxybenzenesulfonamide, 20.24 g (0.20 mol) of triethylamine and 320 ml of methylene chloride and cooled to 0° C. over a period of approximately 20 minutes. The mixture was then stirred for another 1.5 hours with cooling, washed three times with water, dried over magnesium sulfate and concentrated in vacuo in a warm water bath. The resultant oil (Note 1) was cooled and crystallized to an oily solid. Removal of residual solvent with high vacuum caused this material to completely solidify. This solid was recrystallized from 600 ml of cyclohexane with filtering. Collection of the white solid and drying at room temperature in vacuo gave 38.9 g of N-butyl-4-methacryloyloxybenzenesulfonamide; m.p.=59° to 60° C.

後処理

  1. temperaturewith cooling
  2. washwashed three times with water
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo in a warm water bath
  5. temperatureThe resultant oil (Note 1) was cooled
  6. customcrystallized to an oily solid
  7. customRemoval of residual solvent with high vacuum
  8. customThis solid was recrystallized from 600 ml of cyclohexane
  9. filtrationwith filtering
  10. customCollection of the white solid
  11. customdrying at room temperature in vacuo

出典と根拠

ORDレコード
ord-593e6f0fef2f43f194cefeff301ba1ef
出典データセット
uspto-grants-1982_06
特許番号
US04335254

反応ノート

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