Chlorosulfamic acid → 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol

HRID 1973472ノート

反応式

HRID 1973472 の反応式
[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:10][OH:11])[CH2:8][OH:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[S:20](Cl)(=[O:23])(=[O:22])[NH2:21]>C(COC)OC>[C:1]1([C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)([CH2:8][O:9][S:20](=[O:23])(=[O:22])[NH2:21])[CH2:10][O:11][S:20](=[O:23])(=[O:22])[NH2:21])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

参加物

5

反応物 3

HCID 24499Chlorosulfamic acidHCID 24758Sodium hydrideHCID 4104452,2-Diphenylpropane-1,3-diol

生成物 1

HCID 203689762,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol

試薬・触媒・溶媒 1

HCID 80711,2-Dimethoxyethane溶媒3 回

反応条件

温度
4 °C

実験手順

To a solution of 17.3 g. (0.076 mol.) of 2,2-diphenyl-1,3-propanediol in 200 ml. of dimethoxyethane is added 12.7 g. (0.3 mol.) of 57% sodium hydride followed by an additional 400 ml. of dimethoxyethane. After stirring overnight the suspension is cooled to 4° C. A solution of 31.2 g. (0.27 mol.) of sulfamoyl chloride in 600 ml. of dimethoxyethane is then added dropwise. The suspension is stirred overnight at room temperature. After filtering the mixture the filtrate is concentrated and the residue washed with heptane. Chromatography on SilicAR, CC-7, followed by crystallization affords 2,2-diphenyl-1,3-bis-O-sulfamyl-1,3-propanediol.

後処理

  1. stirringThe suspension is stirred overnight at room temperature
  2. filtrationAfter filtering the mixture the filtrate
  3. concentrationis concentrated
  4. washthe residue washed with heptane
  5. customChromatography on SilicAR, CC-7, followed by crystallization

出典と根拠

ORDレコード
ord-230138b3642e4da3b310957da7f385ae
出典データセット
uspto-grants-1976_12
特許番号
US03997585

反応ノート

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