Acetoxyacetyl chloride → Methyl N-[2-(acetyloxy)acetyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate

HRID 485382Notes

Reaction equation

HRID 485382 reaction equation
I.[CH3:2][N:3]([C:12]([S:14][CH3:15])=[NH:13])[N:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[C:16]([O:19][CH2:20][C:21](Cl)=[O:22])(=[O:18])[CH3:17]>C(=O)([O-])[O-].[K+].[K+].CC(C)=O>[C:16]([O:19][CH2:20][C:21]([N:13]=[C:12]([N:3]([CH3:2])[N:4]=[CH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[S:14][CH3:15])=[O:22])(=[O:18])[CH3:17]

Participants

5

Reactant 2

HCID 26297Acetoxyacetyl chlorideHCID 70433894Methyl-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate-hydroiodide

Product 1

HCID 53735339Methyl N-[2-(acetyloxy)acetyl]-1-methyl-2-(phenylmethylene)hydrazinecarboximidothioateYield 82.2%

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 11430Potassium CarbonateSolvent2×

Procedure

Methyl 1-methyl-2-(phenylmethylene)hydrazinecarboximidothioate, hydroiodide (1.34 g) was dissolved in saturated potassium carbonate solution and extracted with ether. The combined organic extracts were dried and evaporated to give an off-white solid which was dissolved in acetone (25 ml) and treated with potassium carbonate (1.1 g) followed by (acetyloxy)acetyl chloride (0.85 g). The suspension was stirred at room temperature for 2 h and evaporated in vacuo. The residue was suspended in water (50 ml) and filtered to give the title compound (1.01 g) which was recrystallised from ethanol, m.p. 115°-117°.

Workup

  1. extractionextracted with ether
  2. customThe combined organic extracts were dried
  3. customevaporated
  4. customto give an off-white solid which
  5. customevaporated in vacuo
  6. filtrationfiltered

Sources & evidence

ORD record
ord-172b7125eb8e402e8dadd17d99ba3f16
Source dataset
uspto-grants-1985_08
Patent number
US04536508

Reaction notes

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