Triethylamine → HCID 22012947, compound

HRID 1533439Notes

Reaction equation

HRID 1533439 reaction equation
Cl[S:2]([C:5]1[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([OH:12])=[O:11])(=[O:4])=[O:3].[CH3:15][N:16]1[CH2:21][CH2:20][NH:19][CH2:18][CH2:17]1.C(N(CC)CC)C>CC(C)=O>[F:14][C:8]1[CH:7]=[CH:6][C:5]([S:2]([N:19]2[CH2:20][CH2:21][N:16]([CH3:15])[CH2:17][CH2:18]2)(=[O:4])=[O:3])=[CH:13][C:9]=1[C:10]([OH:12])=[O:11]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 531671-MethylpiperazineHCID 6089842-Fluoro-5-chlorosulfonylbenzoic acid

Product 1

HCID 22012947HCID 22012947, compoundYield 24.2%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 5-chlorosulphonyl-2-fluorobenzoic acid (47.72 g, 0.2 mol) in acetone (250 ml) was added to a mixture of N-methylpiperazine (22.04 g, 0.22 mol) and triethylamine (24.29 g, 0.24 mol) and the reaction was stirred at ambient for three hours. The mixture was filtered, the resulting solid was recrystallised from water to afford the title compound (14.63 g, 24.2%) as a white solid. δ (DMSO): 2.30 (3H, s), 2.58 (4H, m), 2.95 (4H, m), 7.52 (1H, m), 7.90 (1H, m), 8.10 m/z (Found: 303 [M+H]+, 100%, C12H16FN2O4S requires 303).

Workup

  1. filtrationThe mixture was filtered
  2. customthe resulting solid was recrystallised from water

Sources & evidence

ORD record
ord-5411f7bd0b214b2bab1149423a5fd80f
Source dataset
uspto-grants-2001_03
Patent number
US06207829B1

Reaction notes

Loading…