Water → 2-(2-Acetylhydrazino)-5-(2-methylphenyl)-1,3,4-thiadiazole

HRID 25957Notes

Reaction equation

HRID 25957 reaction equation
Cl.[NH:2]([C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:7][N:8]=1)[NH2:3].O.[C:17](OC(=O)C)(=[O:19])[CH3:18]>N1C=CC=CC=1>[C:17]([NH:3][NH:2][C:4]1[S:5][C:6]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[CH3:15])=[N:7][N:8]=1)(=[O:19])[CH3:18]

Participants

5

Reactant 3

HCID 962WaterHCID 7918Acetic AnhydrideHCID 30501311,3,4-Thiadiazol-2(3H)-one, 5-(2-methylphenyl)-, hydrazone, monohydrochloride

Product 1

HCID 136840272-(2-Acetylhydrazino)-5-(2-methylphenyl)-1,3,4-thiadiazole

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-hydrazino-5-(2-methylphenyl)-1,3,4-thiadiazole hydrochloride (1.0 g) in a mixture of acetic anhydride (0.5 ml) and pyridine (0.5 ml) was kept at room temperature under nitrogen for 0.5 hr. The solution was poured into water (100 ml) and extracted three times with methylene chloride. The organic layer was evaporated and the residue was fractionated on two 20 × 20 cm, 2 mm thick silica preparative t.l.c. plates by eluting with chloroform-methanol (4:1). The resultant product was crystallised from ethyl acetate (0.32 g; 31%) m.p. 165°-6°. C11H12N4OS requires C, 52.8; H, 5.6; N, 22.4; S, 12.8 Found C, 52.8; H, 5.1; N, 22.8; S, 13.2%

Workup

  1. extractionextracted three times with methylene chloride
  2. customThe organic layer was evaporated
  3. washplates by eluting with chloroform-methanol (4:1)
  4. customThe resultant product was crystallised from ethyl acetate (0.32 g; 31%) m.p. 165°-6°

Sources & evidence

ORD record
ord-2c5a6dd7d1a84bc39915fb88606761fb
Source dataset
uspto-grants-1979_04
Patent number
US04147794

Reaction notes

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