Sodium Hydroxide → HCID 136348379, compound

HRID 1777072Notes

Reaction equation

HRID 1777072 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6](/[CH:8]=[C:9](\[CH3:12])/[CH:10]=O)[CH:7]=1.CC1C=CC(S([NH:24][NH2:25])(=O)=O)=CC=1.[OH-].[Na+].[O:28]1[CH2:33][CH2:32][N:31]([S:34]([C:37]2[CH:38]=[C:39]([CH:43]=[CH:44][CH:45]=2)[C:40](Cl)=[O:41])(=[O:36])=[O:35])[CH2:30][CH2:29]1>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:13])=[C:6]([C:8]2[C:9]([CH3:12])=[CH:10][N:25]([C:40]([C:39]3[CH:43]=[CH:44][CH:45]=[C:37]([S:34]([N:31]4[CH2:32][CH2:33][O:28][CH2:29][CH2:30]4)(=[O:36])=[O:35])[CH:38]=3)=[O:41])[N:24]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 14798Sodium Hydroxide2×HCID 15303P-ToluenesulfonylhydrazideHCID 54267581613317-59-1HCID 18801891HCID 18801891, compound

Product 1

HCID 136348379HCID 136348379, compoundYield 31.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A mixture of (E)-3-(5-chloro-2-hydroxyphenyl)-2-methylacrylaldehyde (40 mg, 0.203 mmol) and 4-methylbenzenesulfonohydrazide (41.7 mg, 0.224 mmol) in Acetonitrile (3 mL) were stirred at room temperature for 3 h and then acetonitrile (2 mL), Sodiumhydroxide (8.95 mg, 0.224 mmol) were added and the mixture was heated at reflux for 16 h, then Sodiumhydroxide (12.21 mg, 0.305 mmol) and 3-(morpholinosulfonyl)benzoyl chloride (88 mg, 0.305 mmol) (made from 3-(morpholinosufonyl)benzoic acid) were subsequently added and the mixture was stirred at room temperature for 2 h. Reaction was monitored by TLC. After completion of the reaction, the product was extracted with EtOAc and the organic layer was washed with brine, dried over anhydrous Na2SO4, filtered, and solvent was removed by vacuum. The resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2) afforded the desired product (3-(5-chloro-2-hydroxyphenyl)-4-methyl-1H-pyrazol-1-yl)(3-(morpholinosulfonyl)phenyl)methanone (30 mg, 0.064 mmol, 31.3% yield) as a solid. 1HNMR (400 MHz, CDCl3): δ 8.28 (m, 2H), 8.20 (d, 1H, J=8.0 Hz), 7.95 (d, 1H, J=8.4 Hz), 7.70 (t, 1H, J=7.6 Hz), 7.59 (d, 1H, J=2.4 Hz), 7.18 (dd, 1H, J=2.8 & 8.8 Hz), 6.87 (d, 1H, J=8.4 Hz), 3.68 (m, 4H), 3.02 (m, 4H), 2.40 (s, 3H). ESI-MS: 462.0 [M+H]+

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 16 h
  3. stirringthe mixture was stirred at room temperature for 2 h
  4. customReaction
  5. customAfter completion of the reaction
  6. extractionthe product was extracted with EtOAc
  7. washthe organic layer was washed with brine
  8. dry with materialdried over anhydrous Na2SO4
  9. filtrationfiltered
  10. customsolvent was removed by vacuum
  11. customThe resulting crude material was purified by flash column chromatography (2% CH3OH/CH2Cl2)

Sources & evidence

ORD record
ord-4edcf96539fa4ca3bc0960f69f92b27f
Source dataset
uspto-grants-2016_02
Patent number
US09266838B2

Reaction notes

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