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

HRID 616732Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 616732
[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

Komponenten

5

Edukt 3

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

Produkt 1

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

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 80711,2-DimethoxyethaneLösungsmittel3×

Reaktionsbedingungen

Temperatur
4 °C

Versuchsvorschrift

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.

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-27dc1023de57456fa0b05d978b1b65c9
Quelldatensatz
uspto-grants-1978_02
Patentnummer
US04075351

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