Tetrahydrofuran → 2-Oxocyclohexane-1-sulfonamide

HRID 1906303Notes

Reaction equation

HRID 1906303 reaction equation
O1CCN([C:7]2[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]=2)CC1.[S:13](Cl)(=[O:16])(=[O:15])[NH2:14].C(N(CC)CC)C.[O:25]1CCCC1>>[O:25]=[C:7]1[CH2:12][CH2:11][CH2:10][CH2:9][CH:8]1[S:13]([NH2:14])(=[O:16])=[O:15]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-

Product 1

HCID 133989752-Oxocyclohexane-1-sulfonamide

Procedure

A solution of 16.7 g (0.1 mol) of morpholinocyclohexene in 200 ml of tetrahydrofuran was treated simultaneously, over a period of 2 hours, at -50° C., with solutions of 12.7 g (0.11 mol) of sulfamoyl chloride and 11.1 g (0.11 mol) of triethylamine each in 100 ml of tetrahydrofuran, the mixture was brought from -50° to 20° C. over a period of 2 hours and filtered, the filtrate was evaporated to dryness in vacuo and the residue was chromatographed on 400 g of silica gel with methylene chloride. After recrystallization from isopropanol, the main fraction yielded 9.7 g (54.8% of theory, based on enamine) of 2-oxocyclohexanesulfonamide of melting point 118°-119° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. customthe residue was chromatographed on 400 g of silica gel with methylene chloride
  4. customAfter recrystallization from isopropanol
  5. customthe main fraction yielded 9.7 g (54.8% of theory, based on enamine) of 2-oxocyclohexanesulfonamide of melting point 118°-119° C.

Sources & evidence

ORD record
ord-44ef1ede196f46719426678601c157b0
Source dataset
uspto-grants-1987_03
Patent number
US04650902

Reaction notes

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