Water → 4-(3-Hexyl-2-imidazolon-1-yl)phenylsulphonyl chloride

HRID 863801Notes

Reaction equation

HRID 863801 reaction equation
CO[CH:3](OC)[CH2:4][NH:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[Cl:14][S:15]([C:18]1[CH:23]=[CH:22][C:21]([N:24]=[C:25]=[O:26])=[CH:20][CH:19]=1)(=[O:17])=[O:16].O.FC(F)(F)C(O)=O>C(Cl)Cl>[CH2:6]([N:5]1[CH:4]=[CH:3][N:24]([C:21]2[CH:22]=[CH:23][C:18]([S:15]([Cl:14])(=[O:16])=[O:17])=[CH:19][CH:20]=2)[C:25]1=[O:26])[CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 962WaterHCID 6422Trifluoroacetic acidHCID 81230p-Isocyanatobenzenesulphonyl chlorideHCID 59197986N-(2,2-dimethoxyethyl)hexan-1-amine

Product 1

HCID 194205144-(3-Hexyl-2-imidazolon-1-yl)phenylsulphonyl chlorideYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the amine (38.6 mmol, 7.3 g) in methylene chloride (100 ml) at 0° C. was added 4-(chlorosulphonyl) phenyl isocyanate (38.6 mmol, 8.4 g). The reaction mixture was stirred for 20 mins until a clear solution had formed, and 1:1 water:trifiuoroacetic acid (100 ml total) was added. Vigorous stirring was continued for 16h., the layers separated, the organic layer was diluted with ethyl acetate (500 ml) and washed with saturated sodium bicarbonate solution (4'50 ml), brine (50 ml), dried with anhydrous magnesium sulphate, and concentrated in vacuo. Column chromatrography (eluant 3 hexane/1 ethyl acetate) yielded the title compound as pale yellow crystals (8.8 g, 67%).

Workup

  1. customhad formed
  2. stirringVigorous stirring
  3. waitwas continued for 16h.
  4. customthe layers separated
  5. additionthe organic layer was diluted with ethyl acetate (500 ml)
  6. washwashed with saturated sodium bicarbonate solution (4'50 ml), brine (50 ml)
  7. dry with materialdried with anhydrous magnesium sulphate
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-4b5d44bbbd9b426d99c184a49a22c12c
Source dataset
uspto-grants-1996_10
Patent number
US05561142

Reaction notes

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