Pyridine → HCID 26486858, compound

HRID 1049048Notes

Reaction equation

HRID 1049048 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[S:16]([C:19]1[CH:28]=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][CH:20]=1)(=[O:18])=[O:17]>C(Cl)Cl>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:21]=[CH:20][C:19]([S:16](=[O:17])(=[O:18])[NH:6][C:5]2[CH:7]=[CH:8][C:2]([F:1])=[CH:3][CH:4]=2)=[CH:28][CH:27]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 97314-FluoroanilineHCID 4738388Methyl 4-(Chlorosulfonyl)benzoate

Product 1

HCID 26486858HCID 26486858, compoundYield 77.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-fluoroaniline (484 μL, 5.11 mmol) and pyridine (688 μL, 8.52 mmol) in DCM (20 mL) was treated with methyl 4-(chlorosulfonyl)benzoate (1.00 g, 4.26 mmol) and stirred at room temperature for 3 hours. The mixture was diluted with DCM, washed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine, dried over Na2SO4 and concentrated under vacuum. Triturating with pentane gave 4-(4-fluoro-phenylsulfamoyl)-benzoic acid methyl ester (1.02 g, 77%). 1H NMR (300 MHz, CDCl3) δ 8.10 (d, J=8.4 Hz, 2H), 7.78 (d, J=8.4 Hz, 2H), 7.07-6.99 (m, 2H), 6.98-6.88 (m, 2H), 6.75 (br s, 1H), 3.94 (s, 3H). LCMS (m/z, Method A) ES+ 310.0 [M+1]+.

Workup

  1. washwashed with 1 N aqueous HCl, saturated aqueous NaHCO3, water and brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under vacuum
  4. customTriturating with pentane

Sources & evidence

ORD record
ord-20ee2dced15842f1a02afa03db382657
Source dataset
uspto-grants-2016_07
Patent number
US09382222B2

Reaction notes

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