Tetrahydrofuran → HCID 13398955, compound

HRID 1906305Notes

Reaction equation

HRID 1906305 reaction equation
O1CCN([C:7]([CH2:12][CH2:13][CH2:14][CH3:15])=[CH:8][CH2:9][CH2:10][CH3:11])CC1.N[S:17](Cl)(=[O:19])=[O:18].C([N:23]([CH2:26]C)CC)C.[O:28]1CCCC1>>[CH3:26][NH:23][S:17]([CH:12]([C:7](=[O:28])[CH2:8][CH2:9][CH2:10][CH3:11])[CH2:13][CH2:14][CH3:15])(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 8028Tetrahydrofuran2×HCID 8471TriethylamineHCID 24499Chlorosulfamic acidHCID 56630527HCID 56630527, compound

Product 1

HCID 13398955HCID 13398955, compound

Conditions

Temperature
-40 °C

Procedure

211 g (1 mol) of 5-morpholinonon-4-ene were dissolved in 1 liter of tetrahydrofuran. First 129.5 g (1 mol) of amidosulfonyl chloride in 300 ml of tetrahydrofuran and then 101 g (1 mol) of triethylamine were added dropwise to the solution, cooled to -40° C. The mixture was left to warm up to 20° C. and the precipitated triethylammonium hydrochloride was filtered off. The solvent was then distilled off and the residue was stirred for one hour with a mixture of 1 liter of methylene chloride and 250 ml of 2N hydrochloric acid. The organic phase was separated off, dried with sodium sulfate and distilled. This gave 152.3 g (65% of theory) of a colorless oil of boiling point 135°-138° C. at 0.3 mbar.

Workup

  1. waitThe mixture was left
  2. temperatureto warm up to 20° C.
  3. filtrationthe precipitated triethylammonium hydrochloride was filtered off
  4. distillationThe solvent was then distilled off
  5. customThe organic phase was separated off
  6. dry with materialdried with sodium sulfate
  7. distillationdistilled

Sources & evidence

ORD record
ord-cc9917c9d246422191b2ad63950ac1b9
Source dataset
uspto-grants-1987_03
Patent number
US04650902

Reaction notes

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