Methylamine → 5-(Aminosulfonyl)-2-fluoro-N-methylbenzamide

HRID 1279641Notes

Reaction equation

HRID 1279641 reaction equation
[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10](O)=[O:11])(=[O:4])=[O:3].[CH3:15][NH2:16].O1CCCC1>ClCCl>[NH2:1][S:2]([C:5]1[CH:6]=[CH:7][C:8]([F:14])=[C:9]([CH:13]=1)[C:10]([NH:16][CH3:15])=[O:11])(=[O:4])=[O:3]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 8028TetrahydrofuranHCID 24926842-Fluoro-5-sulfamoylbenzoic acid

Product 1

HCID 230018165-(Aminosulfonyl)-2-fluoro-N-methylbenzamideYield 23%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a suspension of 5-(aminosulfonyl)-2-fluorobenzoic acid [prepared according to Chem. Pharm. Bull. 1995, 43(4), 582-7] (3.0g, 13.7mmol) in dichloromethane (100 mL) at room temperature under nitrogen was added 1-(3-dimethylaminopropyl)-3-ethylcarbodlimide hydrochloride (WSCDI) (2.89 g, 15.06 mmol) followed by a solution of methylamine in tetrahydrofuran (2 M, 8.21 mL, 16.42 mmol), dropwise and the reaction allowed to stir for 16 hours. The crude reaction mixture was then evaporated to dryness and the residue chromatographed on silica gel, eluting with dichloromethane:methanol:ammonia (84:14:2) as solvent to give the amide (732mg, 23%) as a white powder. 1H NMR (300 MHz, d4-MeOH): δ=2.97 (3 H, s), 7.40 (1 H, t), 8.05 (1 H, m), 8.29 (1 H, d). MS m/z 250 (MNH4)+

Workup

  1. customThe crude reaction mixture
  2. customwas then evaporated to dryness
  3. customthe residue chromatographed on silica gel
  4. washeluting with dichloromethane:methanol:ammonia (84:14:2) as solvent

Sources & evidence

ORD record
ord-d40967bfcb5d45eb927e2504369874e2
Source dataset
uspto-grants-2002_09
Patent number
US06448293B1

Reaction notes

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