Acetic Acid → HCID 15631676, compound

HRID 1721938Notes

Reaction equation

HRID 1721938 reaction equation
[C-]#N.[Na+].[Cl:4][C:5]1[C:10]([Cl:11])=[C:9]([O:12]C)[CH:8]=[CH:7][C:6]=1[C:14]([C:16]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[N:19]=[CH:18][CH:17]=1)=[O:15].O.C(O)(=O)C>CS(C)=O>[Cl:11][C:10]1[C:5]([Cl:4])=[C:6]([C:14]([C:16]2[N:20]([CH2:21][C:22]3[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=3)[N:19]=[CH:18][CH:17]=2)=[O:15])[CH:7]=[CH:8][C:9]=1[OH:12]

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 8929Sodium CyanideHCID 14622791HCID 14622791, compound

Product 1

HCID 15631676HCID 15631676, compoundYield 40.6%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
100 °C

Procedure

0.95 g of sodium cyanide is added to a solution of 1.0 g of (2,3-dichloro-4-methoxyphenyl)(1-benzyl-5-pyrazolyl)methanone in dimethylsulfoxide and the mixture is heated at 100° C. for 4 hours under argon gas atmosphere. After cooling, cold water is added to the reaction mixture. The mixture is adjusted to pH 5-6 with acetic acid and then extracted with ethyl acetate. The extract is washed with water, dried and evaporated to remove solvent. The residue is purified by silica gel column chromatography to give 0.39 g of 2,3-dichloro-4-(1-benzyl-5-pyrazolylcarbonyl)phenol.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with water
  4. customdried
  5. customevaporated
  6. customto remove solvent
  7. customThe residue is purified by silica gel column chromatography

Sources & evidence

ORD record
ord-67ea00b4de794293a5a6528b86bda809
Source dataset
uspto-grants-1989_08
Patent number
US04853404

Reaction notes

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