Acetic Acid → HCID 178467061, compound

HRID 37142Notes

Reaction equation

HRID 37142 reaction equation
[NH2:1][C:2]1[C:6]([C:7]2[CH:12]=[CH:11][C:10]([S:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)=[CH:9][CH:8]=2)=[CH:5][NH:4][N:3]=1.C(OC=[CH:24][C:25](=[O:32])[CH2:26][C:27]([O:29]CC)=O)C.[C:33](O)(=O)C>>[OH:29][C:27]1[N:3]2[N:4]=[CH:5][C:6]([C:7]3[CH:8]=[CH:9][C:10]([S:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=4)=[CH:11][CH:12]=3)=[C:2]2[N:1]=[CH:33][C:26]=1[C:25](=[O:32])[CH3:24]

Participants

4

Reactant 3

HCID 176Acetic AcidHCID 54463595Ethyl ethoxymethyleneacetoacetateHCID 178509258HCID 178509258, compound

Product 1

HCID 178467061HCID 178467061, compound

Procedure

A mixture of 534 mg of 3-amino-4-(4-phenylthiophenyl)pyrazole, 484 mg of ethyl ethoxymethyleneacetoacetate, and 15 ml of acetic acid was stirred at room temperature. The precipitate was filtered 30 minutes later, and washed with n-hexane. The mixture of the obtained precipitate, 290 mg of sodium methoxide and 50 ml of toluene was concentrated in vacuo, and 2N hydrochloric acid, methylene chloride and ethyl acetate were added to the residue, and after separating, the organic layer was dried with over anhydrous magnesium sulfate, and concentrated in vacuo. The residue was recrystallized in methylene chloride-ethyl acetate (=1:1), and the title compound was obtained (350 mg)

Workup

  1. filtrationThe precipitate was filtered 30 minutes later
  2. washwashed with n-hexane
  3. additionThe mixture of the obtained precipitate, 290 mg of sodium methoxide and 50 ml of toluene
  4. concentrationwas concentrated in vacuo, and 2N hydrochloric acid, methylene chloride and ethyl acetate
  5. additionwere added to the residue
  6. customafter separating
  7. dry with materialthe organic layer was dried with over anhydrous magnesium sulfate
  8. concentrationconcentrated in vacuo
  9. customThe residue was recrystallized in methylene chloride-ethyl acetate (=1:1)

Sources & evidence

ORD record
ord-a163960e66cc4bcbadb0c17afce45ec1
Source dataset
uspto-grants-1995_05
Patent number
US05420128

Reaction notes

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