P-Toluenesulfonamide → 6-Tosyl-2-oxa-6-azaspiro[3.3]heptane

HRID 1410088

反応式

HRID 1410088 の反応式
[OH-].[K+].[CH3:3][C:4]1[CH:9]=[CH:8][C:7]([S:10]([NH2:13])(=[O:12])=[O:11])=[CH:6][CH:5]=1.Br[CH2:15][C:16]([CH2:21]Br)([CH2:19]Br)[CH2:17][OH:18]>C(O)C>[C:4]1([CH3:3])[CH:5]=[CH:6][C:7]([S:10]([N:13]2[CH2:21][C:16]3([CH2:19][O:18][CH2:17]3)[CH2:15]2)(=[O:12])=[O:11])=[CH:8][CH:9]=1

参加物

5

反応物 3

HCID 6269P-ToluenesulfonamideHCID 14797Potassium HydroxideHCID 15206Pentaerythritol tribromide

生成物 1

HCID 233198916-Tosyl-2-oxa-6-azaspiro[3.3]heptane収率 69.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a solution of KOH (4.98 g, 0.089 mol) and 4-methylbenzenesulfonamide (5.7 g, 0.033 mol) in 90 ml of ethanol, 3-bromo-2,2-bis(bromomethyl)propan-1-ol (9 g, 0.0277 mol) was added at room temperature and the reaction mixture was heated to reflux for 45 h. The solvent was removed by evaporation, 75 ml of 1 M KOH were added and the white suspension was left to stir for another 2 h at room temperature. The mixture was filtered and the white filter cake was rinsed with water until the washing water was neutral. The filter cake was dried under high vacuum to give 4.87 g 6-toluene-4-sulfonyl-2-oxa-6-azaspiro[3.3]heptane (69%) as a white solid. 1H NMR (300 MHz, CDCl3) δ 7.70-7.68 (m, 2H), 7.36-7.34 (m, 2H), 4.58 (s, 4H), 3.90 (s, 4H), 2.45 (s, 3H).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 45 h
  3. customThe solvent was removed by evaporation, 75 ml of 1 M KOH
  4. additionwere added
  5. waitthe white suspension was left
  6. filtrationThe mixture was filtered
  7. washthe white filter cake was rinsed with water until the washing water
  8. customThe filter cake was dried under high vacuum

出典と根拠

ORDレコード
ord-18ab945b6bf84d1985df8941b90708f1
出典データセット
uspto-grants-2014_12
特許番号
US08921383B2

関連ノート

読み込み中…