Cyclohexylamine → 3-(Cyclohexylsulfamoyl)benzoic acid

HRID 916832Notes

Reaction equation

HRID 916832 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>C(Cl)Cl>[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

Conditions

Temperature
0 °C

Procedure

A mixture of 3-(chlorosulfonyl)benzoic acid (2.00 g) and DCM (20 ml) under nitrogen at 0° was treated with cyclohexylamine (3.63 ml) and the mixture was stirred at 0° C. 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. 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.

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
  4. dry with materialThe combined extracts were dried (Na2SO4)
  5. customthe solvent evaporated in vacuo

Sources & evidence

ORD record
ord-cb88d52a0cac4710a6e8101d81bf641a
Source dataset
uspto-grants-2007_09
Patent number
US07271197B2

Reaction notes

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