Acetic Acid → HCID 59631626, compound

HRID 2369024Notes

Reaction equation

HRID 2369024 reaction equation
[F:1][C:2]([F:24])([F:23])[C:3](=O)/[CH:4]=[C:5](\O)/[C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=2)=[CH:9][CH:10]=1.Cl.[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[NH:34][NH2:35].C(O)(=O)C>CN(C=O)C>[Cl:26][C:27]1[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][C:28]=1[N:34]1[C:5]([C:6]2[S:7][C:8]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([S:17]([CH3:20])(=[O:19])=[O:18])[CH:12]=3)=[CH:9][CH:10]=2)=[CH:4][C:3]([C:2]([F:24])([F:23])[F:1])=[N:35]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3084937(2,5-Dichlorophenyl)hydrazine monohydrochlorideHCID 59632486HCID 59632486, compound

Product 1

HCID 59631626HCID 59631626, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
102.5 °C

Procedure

Into an 8 mL vial was weighed 202.7 mg (539 μmol) of (Z)-1,1,1-trifluoro-4-hydroxy-4-(5-(3-(methylsulfonyl)phenyl)thiophen-2-yl)but-3-en-2-one, 117.4 mg (550 μmol) of 2,5-dichlorophenylhydrazine hydrochloride, 3 mL of acetic acid, and 1 mL of DMF. The resulting reaction was stirred at 100-105° C. for 3 h then was concentrated to dryness in vacuo. The residue was purified by silica gel flash chromatography (3×23 cm, 1:1 ethyl acetate-hexanes) and was dried affording the product as a faintly yellow solid, yield: 89 mg (55%). 1H NMR (400 MHz, CDCl3): δ 8.08 (s, 1H), 7.87 (d, J=9 Hz, 1H), 7.75 (d, J=9 Hz, 1H), 7.6 (m, 2H), 7.5 (m, 2H), 7.27 (d, J=4 Hz, 1H), 6.90 (s, 1H), 6.87 (d, J=4 Hz, 1H), 3.09 (s, 3H).

Workup

  1. customThe resulting reaction
  2. concentrationthen was concentrated to dryness in vacuo
  3. customThe residue was purified by silica gel flash chromatography (3×23 cm, 1:1 ethyl acetate-hexanes)
  4. customwas dried
  5. customaffording the product as a faintly yellow solid, yield: 89 mg (55%)

Sources & evidence

ORD record
ord-44dd3fc2e5d9401e8e05c9b041268886
Source dataset
uspto-grants-2014_04
Patent number
US08703805B2

Reaction notes

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