2-Acetoxyisobutyroyl chloride → 1,1-Dimethyl-2-[2-[2-[[4-(methylthio)phenyl]amino]isonicotinoyl]hydrazino]-2-oxoethyl acetate

HRID 452632

Reaction equation

HRID 452632 reaction equation
[CH3:1][S:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][C:10]2[CH:11]=[C:12]([CH:17]=[CH:18][N:19]=2)[C:13]([NH:15][NH2:16])=[O:14])=[CH:5][CH:4]=1.[C:20]([O:23][C:24]([CH3:29])([CH3:28])[C:25](Cl)=[O:26])(=[O:22])[CH3:21]>CN(C)C(=O)C.C(OCC)(=O)C>[C:20]([O:23][C:24]([CH3:29])([CH3:28])[C:25]([NH:16][NH:15][C:13](=[O:14])[C:12]1[CH:17]=[CH:18][N:19]=[C:10]([NH:9][C:6]2[CH:7]=[CH:8][C:3]([S:2][CH3:1])=[CH:4][CH:5]=2)[CH:11]=1)=[O:26])(=[O:22])[CH3:21]

Participants

5

Reactant 2

HCID 1234962-Acetoxyisobutyroyl chlorideHCID 686641102-[[4-(Methylthio)phenyl]amino]isonicotinohydrazide

Product 1

HCID 686646781,1-Dimethyl-2-[2-[2-[[4-(methylthio)phenyl]amino]isonicotinoyl]hydrazino]-2-oxoethyl acetateYield 83%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-[[4-(methylthio)phenyl]amino]isonicotinohydrazide (513 mg, 1.87 mmol) in N,N-dimethylacetamide (5 mL) was added dropwise 2-chloro-1,1-dimethyl-2-oxoethyl acetate (0.294 mL, 2.06 mmol) under ice-cooling, and the resulting mixture was stirred at room temperature for 2 hr. The reaction mixture was diluted with ethyl acetate, washed with water and saturated brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was recrystallized from hexane/ethyl acetate to give the title compound (624 mg, yield 83%) as colorless crystals.

Workup

  1. temperaturecooling
  2. washwashed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue was recrystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-a2830d7d00cf44b386d653326d30cb5e
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Linked notes

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