4-Fluorobenzenesulfonyl chloride → HCID 24962173, compound

HRID 2422819Notes

Reaction equation

HRID 2422819 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=1[C:4]([OH:6])=[O:5].[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19](Cl)(=[O:21])=[O:20])=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Na+].[Na+]>O>[F:12][C:13]1[CH:18]=[CH:17][C:16]([S:19]([NH:1][C:2]2[CH:10]=[CH:9][C:8]([CH3:11])=[CH:7][C:3]=2[C:4]([OH:6])=[O:5])(=[O:21])=[O:20])=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 762552-Amino-5-methylbenzoic acid

Product 1

HCID 24962173HCID 24962173, compoundYield 86.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound was synthesized by reacting 2-amino-5-methylbenzoic acid (0.25 g, 1.65 mmol), 4-fluoro-benzenesulfonyl chloride (0.39 g, 1.98 mmol) and sodium carbonate (0.36 g, 3.39 mmol) in 3 mL of water, following the reaction procedure of 10. The white solid obtained after acidification of reaction mixture was filtered, washed with water and dried to give 12 (0.44 g, 85.42%). Crystallization with EtOH gave (0.3 g) white amorphous solid, mp: 159-160° C.; IR (CHCl3) 3177, 1662, 1342, 1148, 667 cm−1; 1H NMR (500 MHz, CDCl3) δ 2.31 (s, 3H, CH3), 7.08-7.86 (m, 7H, aromatic), 9.32 (br, 1H, NH), and 10.18 (s, 1H, COOH). HRMS calcd 332.0363 (C14H12FNO4S.Na+), found 332.0372.

Workup

  1. customThe title compound was synthesized
  2. customThe white solid obtained
  3. customafter acidification of reaction mixture
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-80b1a2ef115a46f4b08ac556ec45b82d
Source dataset
uspto-grants-2011_06
Patent number
US07960435B2

Reaction notes

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