Methanol → HCID 12050375, compound

HRID 2305329Notes

Reaction equation

HRID 2305329 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([C:6]1[C:7]([F:17])=[C:8]([F:16])[C:9]([F:15])=[C:10]([CH:14]=1)[C:11]([OH:13])=[O:12])(=[O:5])=[O:4].[CH3:19]O>C1(C)C=CC(S(O)(=O)=O)=CC=1>[CH3:19][O:12][C:11](=[O:13])[C:10]1[CH:14]=[C:6]([S:3](=[O:4])(=[O:5])[N:2]([CH3:18])[CH3:1])[C:7]([F:17])=[C:8]([F:16])[C:9]=1[F:15]

Participants

4

Reactant 2

HCID 887MethanolHCID 12050374HCID 12050374, compound

Product 1

HCID 12050375HCID 12050375, compoundYield 10%

Reagents, catalysts & solvents 1

HCID 6101p-Toluenesulfonic acidCatalyst

Procedure

The solid 5-dimethylsulfamoyl-2,3,4-trifluoro-benzoic acid (1.47 g, 0.00519 mol) and p-toluenesulfonic acid catalyst (17.1 mg) were dissolved in methanol (125 ml). The stirring mixture was brought to reflux under a nitrogen atmosphere for 51 hours. The reaction mixture was concentrated in vacuo to give a solid. The product was partitioned between diethyl ether (200 ml) and saturated aqueous potassium carbonate (75 ml). The layers were separated and the organic phase was washed with water (75 ml), brine (75 ml), was dried over anhydrous potassium carbonate, and was concentrated in vacuo to afford 0.15 g of an off-white solid; 10% yield; 1H-NMR (400 MHz; CDCl3) δ 8.23-8.19 (m, 1H), 3.92 (s, 3H), 2.83 (s, 6H); 19F-NMR (376 MHz; CDCl3) δ 120.79 to −121.02 (m), −153.69 to −153.80.

Workup

  1. temperatureto reflux under a nitrogen atmosphere for 51 hours
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customto give a solid
  4. customThe product was partitioned between diethyl ether (200 ml) and saturated aqueous potassium carbonate (75 ml)
  5. customThe layers were separated
  6. washthe organic phase was washed with water (75 ml), brine (75 ml)
  7. dry with materialwas dried over anhydrous potassium carbonate
  8. concentrationwas concentrated in vacuo

Sources & evidence

ORD record
ord-f99024b9404c449f87035834aaa35f2a
Source dataset
uspto-grants-2002_08
Patent number
US06440966B1

Reaction notes

Loading…