Cyclopropylamine → 4-(Cyclopropylsulfamoyl)benzoic acid

HRID 713039Notes

Reaction equation

HRID 713039 reaction equation
Cl[S:2]([C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH:14]1([NH2:17])[CH2:16][CH2:15]1>ClCCl>[CH:14]1([NH:17][S:2]([C:5]2[CH:13]=[CH:12][C:8]([C:9]([OH:11])=[O:10])=[CH:7][CH:6]=2)(=[O:4])=[O:3])[CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 11341514-(Cyclopropylsulfamoyl)benzoic acidYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-chlorosulfonylbenzoic acid (10.0 g, 45.3 mmol) in dichloromethane (350 mL) at 0° C. was added cyclopropanamine (15.5 g, 19 mL, 271.9 mmol). The reaction mixture was allowed to warm to room temperature over 16 hours. The solvent was evaporated under reduced pressure. The residue was dissolved in water (150 mL) and acidified using hydrochloric acid. The aqueous layer was extracted with EtOAc (2×200 mL). The organic layer was dried over sodium sulfate, filtered and concentrated in vacuo to give 4-(cyclopropylsulfamoyl)benzoic acid (10.0 g, 92%) as a white solid. ESI-MS m/z calc. 241.0. found 242.5 (M+1)+; Retention time: 0.84 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.27 (s, 1H), 7.97 (d, J=8.3 Hz, 2H), 7.91 (d, J=2.5 Hz, 1H), 7.75 (d, J=8.3 Hz, 2H), 2.03-1.90 (m, 1H), 0.38-0.28 (m, 2H), 0.23-0.15 (m, 2H).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in water (150 mL)
  3. extractionThe aqueous layer was extracted with EtOAc (2×200 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-bc38b9511bcc4276831727bed28c3d99
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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