Cyclohexylamine → 3-(Cyclohexylsulfamoyl)benzoic acid

HRID 219027

Reaction equation

HRID 219027 reaction equation
Cl[S:2]([C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=1)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3].[CH:14]1([NH2:20])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[CH:14]1([NH:20][S:2]([C:5]2[CH:6]=[C:7]([CH:11]=[CH:12][CH:13]=2)[C:8]([OH:10])=[O:9])(=[O:4])=[O:3])[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 7965CyclohexylamineHCID 77641Benzoic acid, 3-(chlorosulfonyl)-

Product 1

HCID 7791083-(Cyclohexylsulfamoyl)benzoic acid

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 3-(chlorosulfonyl)benzoic acid (2.00 g) and dichloromethane (20 ml) under nitrogen at 0° was treated with cyclohexylamine (3.63 ml) and the mixture was stirred at 0° for 0.5 h. The solvent was evaporated in vacuo and the residue was treated with 1M potassium hydrogen sulfate solution (50 ml) and extracted with EtOAc (3×50 ml). The combined extracts were dried (Na2SO4) and the solvent evaporated in vacuo to give the title compound (2.28 g). LCMS RT=3.16 min, ES+ve 284 (MH)+.

Workup

  1. customThe solvent was evaporated in vacuo
  2. additionthe residue was treated with 1M potassium hydrogen sulfate solution (50 ml)
  3. extractionextracted with EtOAc (3×50 ml)
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-f2a748655b484ceabeb958fa2a926dc9
Source dataset
uspto-grants-2012_06
Patent number
US08198483B2

Linked notes

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