Pyrrolidine → 4-(Pyrrolidine-1-sulfonyl)benzoic acid

HRID 713059Notes

Reaction equation

HRID 713059 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].[NH:14]1[CH2:18][CH2:17][CH2:16][CH2:15]1>ClCCl>[N:14]1([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])[CH2:18][CH2:17][CH2:16][CH2:15]1

Participants

4

Reactant 2

HCID 31268PyrrolidineHCID 823854-(Chlorosulfonyl)benzoic acid

Product 1

HCID 7636514-(Pyrrolidine-1-sulfonyl)benzoic acidYield 30.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-chlorosulfonylbenzoic acid (2 g, 9.07 mmol) in dichloromethane (10 mL) was added a solution of pyrrolidine (1.29 g, 1.51 mL, 18.1 mmol) in dichloromethane (10 mL) and the reaction mixture was stirred at room temperature for 24 hours. The reaction mixture was filtered and the white solid obtained was washed with water (50 ml) and diethyl ether (10 ml) and dried under vacuum to give 4-pyrrolidin-1-ylsulfonylbenzoic acid (700 mg, 30%). ESI-MS m/z calc. 255.0. found 256.3 (M+1)+; Retention time: 1.18 minutes (3 min run); 1H NMR (400 MHz, DMSO) δ 13.49 (s, 1H), 8.15 (d, J=8.5 Hz, 2H), 7.92 (d, J=8.5 Hz, 2H), 3.17 (t, J=6.7 Hz, 4H), 1.65 (t, J=6.7 Hz, 4H).

Workup

  1. filtrationThe reaction mixture was filtered
  2. customthe white solid obtained
  3. washwas washed with water (50 ml) and diethyl ether (10 ml)
  4. customdried under vacuum

Sources & evidence

ORD record
ord-7de7e0a999c24182b69181e379a81d9b
Source dataset
uspto-grants-2015_11
Patent number
US09181273B2

Reaction notes

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