Tetrahydrofuran → HCID 13398979, compound

HRID 1906304Notes

Reaction equation

HRID 1906304 reaction equation
[CH:1]1([NH:7][S:8](Cl)(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O1CCN([C:18]2[CH2:23][CH2:22][CH2:21][CH2:20][CH:19]=2)CC1.C(N(CC)CC)C.[O:31]1CCCC1>>[CH:1]1([NH:7][S:8]([CH:19]2[CH2:20][CH2:21][CH2:22][CH2:23][C:18]2=[O:31])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 69589Morpholine, 4-(1-cyclohexen-1-yl)-HCID 12914615Cyclohexylsulfamyl chloride

Product 1

HCID 13398979HCID 13398979, compoundYield 57.4%

Procedure

20.8 g (0.105 mol) of cyclohexylaminosulfonyl chloride in 60 ml of tetrahydrofuran were added dropwise, over a period of 2 hours, at -50° C., to a solution of 16.7 g (0.1 mol) of morpholinocyclohex-1-ene and 10.6 g (0.105 mol) of triethylamine in 150 ml of tetrahydrofuran, the mixture was brought to 20° C. over a period of 4 hours and filtered, the filtrate was evaporated to dryness in vacuo and the residue was chromatographed on 80 g of silica gel with methylene chloride. After crystallization from diisopropyl ether, the main fraction yielded 14.9 g (57.4%) of colorless crystals of melting point 105°-109° C.

Workup

  1. filtrationfiltered
  2. customthe filtrate was evaporated to dryness in vacuo
  3. customthe residue was chromatographed on 80 g of silica gel with methylene chloride
  4. customAfter crystallization from diisopropyl ether

Sources & evidence

ORD record
ord-b61acfdeb8734845963ca749231bb66d
Source dataset
uspto-grants-1987_03
Patent number
US04650902

Reaction notes

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