Methanol → HCID 25138305, compound

HRID 1511499Notes

Reaction equation

HRID 1511499 reaction equation
CO.[F:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]([C:23]2[S:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[C:24]=2[CH3:32])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([O:21]C)=[O:20])=[CH:15][CH:14]=2)(=[O:12])=[O:11])=[CH:6][C:5]=1[C:35]([F:38])([F:37])[F:36].[OH-].[Na+]>CCOC(C)=O.Cl>[F:3][C:4]1[CH:34]=[CH:33][C:7]([CH2:8][N:9]([C:23]2[S:27][C:26]3[CH:28]=[CH:29][CH:30]=[CH:31][C:25]=3[C:24]=2[CH3:32])[S:10]([C:13]2[CH:18]=[CH:17][C:16]([C:19]([OH:21])=[O:20])=[CH:15][CH:14]=2)(=[O:11])=[O:12])=[CH:6][C:5]=1[C:35]([F:38])([F:36])[F:37]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 56723940Methyl 4-({[4-fluoro-3-(trifluoromethyl)phenyl]methyl}(3-methyl-1-benzothiophen-2-yl)sulfamoyl)benzoate

Product 1

HCID 25138305HCID 25138305, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

A 3-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, condenser and thermocouple was charged with MeOH (1.9 L) and N-[4-fluoro-3-(trifluoromethyl)-benzyl]-N-(3-methylbenzo[b]thiophen-2-yl)-4-carbomethoxy-benzenesulfonamide (190 g, 0.35 mol) followed by 3M NaOH (412 mL, 1.2 mol) and the resulting mixture refluxed for 2 h. The resulting mixture was then cooled to room temperature, diluted with EtOAc (2 L) and 1N HCl (2 L), the layers separated and the aqueous phase extracted with EtOAc (2 L). The organic extracts were combined, washed with brine (1.5 L), dried over Na2SO4, filtered and evaporated under reduced pressure to yield a yellow solid. The yellow solid was placed in vacuum oven for 18 h at 50° C. to yield N-[4-fluoro-3-(trifluoromethyl)-benzyl]-N-(3-methylbenzo[b]thiophen-2-yl)-4-carboxy-benzenesulfonamide as a yellow solid. 1H-NMR (DMSO-d6) δ 13.63 (s, 1H), 8.19 (d, 2H), 8.01 (d, 2H), 7.86-7.83 (m, 1H), 7.71-7.63 (m, 3H), 7.49-7.37 (M, 3H), 4.89 (br s, 1H), 1.95 (s, 3H).

Workup

  1. customA 3-L 4-neck flask equipped with an overhead mechanical stirrer, N2 inlet/outlet adapter, condenser
  2. temperaturethe resulting mixture refluxed for 2 h
  3. customthe layers separated
  4. extractionthe aqueous phase extracted with EtOAc (2 L)
  5. washwashed with brine (1.5 L)
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. customevaporated under reduced pressure
  9. customto yield a yellow solid

Sources & evidence

ORD record
ord-f27179c966f4471db5811c30730121b7
Source dataset
uspto-grants-2012_07
Patent number
US08216547B2

Reaction notes

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