Sodium Methoxide → HCID 178494431, compound

HRID 1385288Notes

Reaction equation

HRID 1385288 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2=[C:7]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)[S:8][C:9](S(C)=O)=[C:5]2[C:4](=[O:19])[CH2:3]1.[CH3:21][O-:22].[Na+]>CO>[CH3:1][C:2]1([CH3:20])[CH2:18][C:6]2=[C:7]([C:13]3[CH:17]=[CH:16][NH:15][N:14]=3)[S:8][C:9]([O:22][CH3:21])=[C:5]2[C:4](=[O:19])[CH2:3]1

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 178504628HCID 178504628, compound

Product 1

HCID 178494431HCID 178494431, compoundYield 15%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Conditions

Temperature
70 °C

Procedure

To a stirred solution of 6,6-dimethyl-3-methanesulphinyl-1-(pyrazol-3-yl)-4,5,6,7-tetrahydrobenzo[c]thiophen-4-one (80 mg, 0.26 mmol) in methanol (3 mL) was added a solution of sodium methoxide in methanol (1.0 mL of a 0.5M solution, 0.5 mmol). The solution was heated at 70° C. for 24 h. after which time the mixture was cooled to room temperature and partitioned between EtOAc (2×20 mL) and water (20 mL). The combined organic layers were dried (Na2SO4) and evaporated. The residue was chromatographed on silica gel, eluting with CH2Cl2:MeOH (95:5), to give the title compound (11 mg, 15%) as a pale yellow solid. mp 202-204° C. Found: C, 60.24; H, 5.66; N, 10.06%. C14H16N2O2S.0.1 (H2O) requires: C, 60.45; H, 5.87; N, 10.07%. 1HNMR (360 MHz, d6-DMSO)δ 0.98 (6H, s), 2.27 (2H, s), 2.79 (2H, s), 4.03 (3H, s), 6.54 (1H, br s), 7.81 (1H, br s), 12.92 (1H, br s). MS (ES+) 277 (M+1).

Workup

  1. temperaturewas cooled to room temperature
  2. custompartitioned between EtOAc (2×20 mL) and water (20 mL)
  3. dry with materialThe combined organic layers were dried (Na2SO4)
  4. customevaporated
  5. customThe residue was chromatographed on silica gel
  6. washeluting with CH2Cl2:MeOH (95:5)

Sources & evidence

ORD record
ord-ec7263a6fc894a2db9dcacb18cb8fbb8
Source dataset
uspto-grants-2001_07
Patent number
US06262103B1

Reaction notes

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