Methyl iodide → HCID 21326076, compound

HRID 25958Notes

Reaction equation

HRID 25958 reaction equation
[C:1]([NH:4][NH:5][C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:9][N:10]=1)(=[O:3])[CH3:2].[Na].[CH3:19]I>C(O)C>[C:1]([N:4]([CH3:19])[NH:5][C:6]1[S:7][C:8]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[CH3:17])=[N:9][N:10]=1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 5360545SodiumHCID 136840272-(2-Acetylhydrazino)-5-(2-methylphenyl)-1,3,4-thiadiazole

Product 1

HCID 21326076HCID 21326076, compoundYield 68.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

2-(2-Acetylhydrazino)-5-(2-methylphenyl)-1,3,4-thiadiazole (6.30 g) was added to a stirred solution of sodium (0.57 g) in ethanol (63 ml) at room temperature. After 15 minutes methyl iodide (7.10 g) was added and the solution kept at room temperature for 31/2 hours. The solvent was removed in vacuo and the residue chromatographed on a silica column (315 g) using mixtures of methanol and chloroform, finally eluting with 5% methanolchloroform. The resultant product was crystallised from ethyl acetate to give 2-(2-acetyl-2-methylhydrazino)-5-(2-methylphenyl)-1,3,4-thiadiazole (4.57 g) m.p. 106°-8°.

Workup

  1. customkept at room temperature for 31
  2. custom2 hours
  3. customThe solvent was removed in vacuo
  4. customthe residue chromatographed on a silica column (315 g)
  5. washfinally eluting with 5% methanolchloroform
  6. customThe resultant product was crystallised from ethyl acetate

Sources & evidence

ORD record
ord-d01c492ba6924303b2dda064df2f2ee0
Source dataset
uspto-grants-1979_04
Patent number
US04147794

Reaction notes

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