4-Fluorobenzenesulfonyl chloride → HCID 24961447, compound

HRID 2422820Notes

Reaction equation

HRID 2422820 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=1>N1C=CC=CC=1>[F:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:1][C:2]2[CH:9]=[C:8]([CH3:10])[CH:7]=[CH:6][C:3]=2[C:4]#[N:5])(=[O:20])=[O:19])=[CH:14][CH:13]=1

Participants

4

Reactant 2

HCID 95884-Fluorobenzenesulfonyl chlorideHCID 28012762-Amino-4-methylbenzonitrile

Product 1

HCID 24961447HCID 24961447, compoundYield 43.7%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

The title compound was synthesized by reacting 2-amino-4-methylbenzonitrile (0.25 g, 1.89 mmol) and 4-fluoro-benzenesulphonyl chloride (0.37 g, 1.89 mmol) in 2 mL of dry pyridine, following the reaction procedure of 6.29 The concentrated reaction mixture was poured into ice cold water (300 mL), and resulting pale white solid was filtered, washed with water and dried to gave 13 (0.24 g, 42.8%). Crystallization with EtOH gave (0.15 g) white amorphous solid, mp: 130-132° C.; IR (CHCl3) 3260, 2226, 1376, 1340, 1171, 1156 cm−1; 1H NMR (500 MHz, CDCl3) δ 2.42 (s, 3H, CH3) and 6.90-7.83 (m, 7H, aromatic). HRMS calcd 313.0417 (C14H11FN2O2S.Na+), found 313.0418.

Workup

  1. customThe title compound was synthesized
  2. customthe reaction procedure of 6.29
  3. customThe concentrated reaction mixture
  4. customresulting pale white solid
  5. filtrationwas filtered
  6. washwashed with water
  7. customdried

Sources & evidence

ORD record
ord-24668b27271a406db18d2cf68f4bef74
Source dataset
uspto-grants-2011_06
Patent number
US07960435B2

Reaction notes

Loading…