Methanol → Methyl 4-({[4-fluoro-3-(trifluoromethyl)phenyl]methyl}(3-methyl-1-benzothiophen-2-yl)sulfamoyl)benzoate

HRID 1691574Notes

Reaction equation

HRID 1691574 reaction equation
[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[CH3:29])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([OH:19])=[O:18])=[CH:13][CH:12]=2)(=[O:10])=[O:9])=[CH:4][C:3]=1[C:32]([F:35])([F:34])[F:33].[CH3:36]O.[OH-].[Na+]>CCOC(C)=O.Cl>[F:1][C:2]1[CH:31]=[CH:30][C:5]([CH2:6][N:7]([C:20]2[S:24][C:23]3[CH:25]=[CH:26][CH:27]=[CH:28][C:22]=3[C:21]=2[CH3:29])[S:8]([C:11]2[CH:16]=[CH:15][C:14]([C:17]([O:19][CH3:36])=[O:18])=[CH:13][CH:12]=2)(=[O:9])=[O:10])=[CH:4][C:3]=1[C:32]([F:35])([F:33])[F:34]

Participants

6

Reactant 3

HCID 887MethanolHCID 14798Sodium HydroxideHCID 25138305HCID 25138305, compound

Product 1

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

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 8857Ethyl AcetateSolvent

Procedure

N-[4-Fluoro-3-(trifluoromethyl)-benzyl]-N-(3-methylbenzo[b]thiophen-2-yl)-4-carboxy-benzenesulfonamide (not shown). 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 compound 141 (190 g, 0.35 mol) followed by 3M NaOH (412 mL, 1.2 mol) and the reaction mixture was refluxed for 2 h. The reaction mixture was 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. The yellow solid was placed in vacuum oven for 18 h at 50° C. to afford 158 g of the titled compound (not shown) 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 reaction mixture was 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

Sources & evidence

ORD record
ord-eb75257138d54281b12d6ad032b9727f
Source dataset
uspto-grants-2012_04
Patent number
US08153682B2

Reaction notes

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