Hydrazinecarbothioamide, N-phenyl- → 3-Anilino-4-acetyl-5-methylpyrazole

HRID 223416

Reaction equation

HRID 223416 reaction equation
[C:1]1([NH:7][C:8](=S)[NH:9][NH2:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.Cl[CH2:13][C:14]([CH2:16][C:17](=O)[CH3:18])=[O:15]>O1CCCC1>[NH:7]([C:8]1[C:16]([C:14](=[O:15])[CH3:13])=[C:17]([CH3:18])[NH:10][N:9]=1)[C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

4

Reactant 2

HCID 730679Hydrazinecarbothioamide, N-phenyl-HCID 144968561-Chloro-2,4-pentanedione

Product 1

HCID 204753773-Anilino-4-acetyl-5-methylpyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

50 g of 4-phenylthiosemicarbazide is suspended in 300 ml of tetrahydrofuran and 0.5 ml of concentrated HCL is added. Then 40.4 g of 3-chloroacetyl acetone is allowed to run in all at once and the whole is cooled with an ice-bath. After 12 hours' stirring, the precipitate formed is suction filtered, washed with acetone and then boiled in a water/acetone mixture (1:1). This hot solution is filtered off from the sulfur and neutralized with aqueous ammonia solution. The product is then suction filtered and recrystallized from acetone; m.p. 246°-247° C.

Workup

  1. addition0.5 ml of concentrated HCL is added
  2. temperatureis cooled with an ice-bath
  3. customthe precipitate formed
  4. filtrationfiltered
  5. washwashed with acetone
  6. filtrationThis hot solution is filtered off from the sulfur and neutralized with aqueous ammonia solution
  7. filtrationsuction filtered
  8. customrecrystallized from acetone

Sources & evidence

ORD record
ord-571d4729c84c4820b9fa50bf881db780
Source dataset
uspto-grants-1982_10
Patent number
US04354031

Linked notes

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