Morpholine → 4-(1H-imidazol-1-ylsulfonyl)morpholine

HRID 1928773

Reaction equation

HRID 1928773 reaction equation
FC(F)(F)S([O-])(=O)=O.[N:9]1([S:14]([N:17]2[CH:21]=[CH:20][NH+:19](C)[CH2:18]2)(=[O:16])=[O:15])[CH:13]=[CH:12]N=[CH:10]1.N1CC[O:26][CH2:25]C1>C(#N)C>[N:17]1([S:14]([N:9]2[CH2:13][CH2:12][O:26][CH2:25][CH2:10]2)(=[O:16])=[O:15])[CH:21]=[CH:20][N:19]=[CH:18]1

Participants

4

Reactant 2

HCID 8083MorpholineHCID 866341663-(1H-Imidazol-1-ylsulfonyl)-1-methyl-1H-imidazolium trifluoromethanesulfonate

Product 1

HCID 7538364-(1H-imidazol-1-ylsulfonyl)morpholineYield 95.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-(1H-Imidazol-1-ylsulfonyl)-1-methyl-1H-imidazolium trifluoromethanesulfonate (1.5 g, 3.0 mmol) was dissolved in acetonitrile (15 mL) and treated with morpholine (0.30 mL, 4.0 mmol) and stirred for 16 h at ambient temperature. The solvent was removed and the residue subjected to column chromatography (silica gel, heptane, ethyl acetate 1:1, 0:1) to yield 4-(imidazole-1-sulfonyl)-morpholine (0.62 g, 83%) as a white solid; MS: m/e=218.5 (M+H+).

Workup

  1. customThe solvent was removed

Sources & evidence

ORD record
ord-084be5e0d8bd47eb9e3ac4f33eaee896
Source dataset
uspto-grants-2012_05
Patent number
US08183380B2

Linked notes

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