Water → HCID 53743045, compound

HRID 1981177Notes

Reaction equation

HRID 1981177 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1CO.[H-].[Na+].[S:11](Cl)(=[O:14])(=[O:13])N.[OH2:16].C[N:18]([CH:20]=O)C>>[CH3:20][NH:18][S:11]([O:14][CH:2]1[CH2:3][CH2:4][CH2:5][CH2:6][O:1]1)(=[O:16])=[O:13]

Participants

6

Reactant 5

HCID 962WaterHCID 6228DimethylformamideHCID 7524Tetrahydropyran-2-methanolHCID 24499Chlorosulfamic acidHCID 24758Sodium hydride

Product 1

HCID 53743045HCID 53743045, compound

Procedure

To a cold solution (-5° C.) of tetrahydropyran-2-methanol (2.33 g, 0.02 mol) in DMF (40 ml) was added 50% oily sodium hydride (1.17 g, 0.024 mol as NaH). After stirring for 45 min, sulfamoyl chloride (3.42 g, 0.03 mol) was added and the stirring continued for an additional 45 min, at -5° C. The reaction mixture was poured into cold water and extracted with chloroform. The organic layer was dried (Na2SO4) and the solvents were removed under vacuum to give a syrup which was dry column chromatographed (eluted with ethyl acetate:hexane, 4:1 v/v) to give pure (tetrahydro-2H-pyran-2-yl) methanesulfamate as a pale yellow syrup, IR:(CHCl3) 1180 cm-1 and 1370 cm-1 (OSO2NH2).

Workup

  1. waitthe stirring continued for an additional 45 min, at -5° C
  2. extractionextracted with chloroform
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. customthe solvents were removed under vacuum
  5. customto give a syrup which
  6. customwas dry column
  7. customchromatographed
  8. wash(eluted with ethyl acetate:hexane, 4:1 v/v)

Sources & evidence

ORD record
ord-51585397f8274e43b5b05ab6d6a07d57
Source dataset
uspto-grants-1985_04
Patent number
US04513006

Reaction notes

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