Sulfuric Acid → HCID 59632294, compound

HRID 2369059Notes

Reaction equation

HRID 2369059 reaction equation
[OH:1]S(O)(=O)=O.[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=3)=[CH:21][CH:22]=2)=[CH:16][C:15]([CH2:33][C:34]#N)=[N:14]1.[C:36]([O-])([O-])=[O:37].[Na+].[Na+]>CO.O.O>[Cl:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N:13]1[C:17]([C:18]2[S:19][C:20]([C:23]3[CH:28]=[CH:27][CH:26]=[C:25]([S:29]([CH3:32])(=[O:31])=[O:30])[CH:24]=3)=[CH:21][CH:22]=2)=[CH:16][C:15]([CH2:33][C:34]([O:37][CH3:36])=[O:1])=[N:14]1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 10340Sodium CarbonateHCID 59633179HCID 59633179, compound

Product 1

HCID 59632294HCID 59632294, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 22242641Methanol--water (1/1)Solvent

Conditions

Temperature
90 °C

Procedure

Concentrated H2SO4 (4 mL) was added dropwise at 0° C. to a stirred solution of the [1-(2-chlorophenyl)-5-{5-[3-(methylsulfonyl)phenyl]-2-thienyl}-1H-pyrazol-3-yl]acetonitrile (148 mg, 0.33 mmol) in a mixture of MeOH—H2O (10:1, 11 mL), and the resulting mixture was stirred at 90° C. overnight. The mixture was diluted with cold water, then basified with Na2CO3 solid, extracted with EtOAc. The combined extracts were washed with brine, dried over Na2SO4, and evaporated in vacuo. The crude product was purified by flash chromatography (0-40% 20% MeOH/DCM) to afford the title compound as a white solid (131 mg, 82%). 1HNMR (CDCl3): δ 8.04 (m, 1H), 7.83-7.81 (m, 1H), 7.73-7.71 (m, 1H), 7.57-7.41 (m, 5H), 7.20 (d, 1H), 6.75 (d, 1H), 6.69 9s, 1H), 3.82 9s, 2H), 3.79 (s, 3H), 3.08 (s, 3H). MS(ES): 487 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. customevaporated in vacuo
  5. customThe crude product was purified by flash chromatography (0-40% 20% MeOH/DCM)

Sources & evidence

ORD record
ord-bbe182e68e9a4c898789c114db40f536
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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