Hydrochloric Acid → N-Cyclohexyl-3-(hydroxymethyl)benzenesulfonamide

HRID 219028

反応式

HRID 219028 の反応式
[CH:1]1([NH:7][S:8]([C:11]2[CH:12]=[C:13]([CH:17]=[CH:18][CH:19]=2)[C:14](O)=[O:15])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.B.C1COCC1.CO.Cl>C1COCC1>[CH:1]1([NH:7][S:8]([C:11]2[CH:19]=[CH:18][CH:17]=[C:13]([CH2:14][OH:15])[CH:12]=2)(=[O:9])=[O:10])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

参加物

6

反応物 4

HCID 313Hydrochloric AcidHCID 887MethanolHCID 7791083-(Cyclohexylsulfamoyl)benzoic acidHCID 2723981Borane;tetrahydrofuran

生成物 1

HCID 65751619N-Cyclohexyl-3-(hydroxymethyl)benzenesulfonamide収率 90.9%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

A solution of 3-[(cyclohexylamino)sulfonyl]benzoic acid (2.25 g) in THF (100 ml) under nitrogen at 0° was treated dropwise with 1M borane-THF solution (23.82 ml). The mixture was stirred at 0° for 0.5 h and then at 20° for 72 h. The mixture was cooled to 0° and MeOH (20 ml) was added dropwise. The mixture was stirred for 15 min and then 2N hydrochloric acid (50 ml) was added and the mixture was allowed to warm to 20°. The bulk of the organic solvents were removed by evaporation in vacuo and the residual aqueous phase was extracted with EtOAc (2×40 ml). The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo. The residue was purified by SPE on alumina (10 g, activated, neutral, Brockmann 1). Elution with MeOH-dichloromethane (1:20) gave the title compound (1.944 g). LCMS RT=2.95 min, ES+ve 270 (MH)+.

後処理

  1. waitat 20° for 72 h
  2. temperatureThe mixture was cooled to 0°
  3. stirringThe mixture was stirred for 15 min
  4. temperatureto warm to 20°
  5. customThe bulk of the organic solvents were removed by evaporation in vacuo
  6. extractionthe residual aqueous phase was extracted with EtOAc (2×40 ml)
  7. dry with materialThe combined extracts were dried (Na2SO4)
  8. customthe solvent evaporated in vacuo
  9. customThe residue was purified by SPE on alumina (10 g, activated, neutral, Brockmann 1)
  10. washElution with MeOH-dichloromethane (1:20)

出典と根拠

ORDレコード
ord-a2efa7f015cb405f968547bf340884f5
出典データセット
uspto-grants-2012_06
特許番号
US08198483B2

関連ノート

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