Propylamine → 2-Chloro-4-fluoro-5-[(propylamino)sulfonyl]benzoic acid

HRID 1992137Notes

Reaction equation

HRID 1992137 reaction equation
ClS(C1C=C(C=CC=1F)C(O)=O)(=O)=O.[CH2:15]([NH2:18])[CH2:16][CH3:17].[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[C:26]([S:30](NCC)(=[O:32])=[O:31])=[CH:25][C:21]=1[C:22]([OH:24])=[O:23]>>[Cl:19][C:20]1[CH:28]=[C:27]([F:29])[C:26]([S:30]([NH:18][CH2:15][CH2:16][CH3:17])(=[O:32])=[O:31])=[CH:25][C:21]=1[C:22]([OH:24])=[O:23]

Participants

4

Reactant 3

HCID 7852PropylamineHCID 39298913-(Chlorosulfonyl)-4-fluorobenzoic acidHCID 587280522-Chloro-5-[(ethylamino)sulfonyl]-4-fluorobenzoic acid

Product 1

HCID 587283362-Chloro-4-fluoro-5-[(propylamino)sulfonyl]benzoic acid

Procedure

2.512 g (9.2 mmol) 3-chlorosulfonyl-4-fluorobenzoic acid was added to 2.27 mL (27.6 mmol) propylamine following the general procedure in for 2-chloro-5-[(ethylamino)sulfonyl]-4-fluorobenzoic acid. Crude product was used in subsequent step without further purification. 1H NMR (300 MHz, DMSO-d6) δ8.19-8.22 (d, 1H, J=7.84 Hz), 8.12-8.16 (t, 1H, J=11.59 Hz), 7.85-7.88 (d, 1H, J=9.90 Hz), 2.80-2.87 (q, 2H, J=6.82), 1.33-1.45 (m, 2H), 0.77-0.82 (t, 3H, J=7.51 Hz).

Workup

  1. customCrude product was used in subsequent step without further purification

Sources & evidence

ORD record
ord-2e500b6bcc5d4913b047762eea91b446
Source dataset
uspto-grants-2010_01
Patent number
US07645771B2

Reaction notes

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