Acetyl chloride → HCID 178469414, compound

HRID 2177722Notes

Reaction equation

HRID 2177722 reaction equation
C(Cl)(=O)C.[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26][CH3:27])[C:18]([C:28]3[N:32](C4CCCCO4)[N:31]=[CH:30][CH:29]=3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1>CO>[C:5]1([S:11]([CH2:14][C:15]2[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])=[C:19]([O:26][CH3:27])[C:18]([C:28]3[CH:29]=[CH:30][NH:31][N:32]=3)=[CH:17][CH:16]=2)(=[O:13])=[O:12])[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 6367Acetyl chlorideHCID 71268997Ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-[1-(tetrahydropyran-2-yl)pyrazol-5-yl]benzoate2×

Product 1

HCID 178469414HCID 178469414, compoundYield 99.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Acetyl chloride (0.1 ml) was added to methanol (10 ml) cooled in ice and the resultant solution was added to ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-[1-(tetrahydropyran-2-yl)pyrazol-5-yl]benzoate (Intermediate 47, 0.05 g). The resultant mixture was stirred at room temperature for 1 hour then evaporated to dryness. The residue was treated with sodium bicarbonate (saturated aqueous solution) and extracted with DCM, dried (MgSO4) and filtered. The filtrate was evaporated to dryness to give ethyl 6-(benzenesulphonylmethyl)-2-methoxy-3-(3-pyrazolyl)benzoate (0.041 g) as a gum.

Workup

  1. temperaturecooled in ice
  2. customthen evaporated to dryness
  3. additionThe residue was treated with sodium bicarbonate (saturated aqueous solution)
  4. extractionextracted with DCM
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customThe filtrate was evaporated to dryness

Sources & evidence

ORD record
ord-9fc4b3acbf2c4ef9b612f2b423b6ba4f
Source dataset
uspto-grants-2015_06
Patent number
US09067905B2

Reaction notes

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