Toluene → 3-Anilino-4-isopropoxycarbonyl-5-methylpyrazole

HRID 443588

Reaction equation

HRID 443588 reaction equation
Cl[CH2:2][C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4].[C:9]1([NH:15][C:16](=S)[NH:17][NH2:18])[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[C:20]1(C)C=CC=C[CH:21]=1>O1CCCC1>[NH:15]([C:16]1[C:2]([C:3]([O:5][CH:6]([CH3:8])[CH3:7])=[O:4])=[C:20]([CH3:21])[NH:18][N:17]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 7759Isopropyl chloroacetateHCID 730679Hydrazinecarbothioamide, N-phenyl-

Product 1

HCID 204753863-Anilino-4-isopropoxycarbonyl-5-methylpyrazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

35.7 g of isopropyl 2-chloroacetate is added to a suspension of 33.5 g of 4-phenylthiosemicarbazide in 150 ml of tetrahydrofuran. After the mixture has been stirred for 30 minutes it is boiled for a further 30 minutes and then allowed to cool. The precipitated solid is isolated by suction filtering, washed with acetone and the residue is heated in a water/acetone mixture (1:1). After the separated sulfur has been poured off, the whole is allowed to cool and is neutralized with aqueous NaHCO3, solution and the precipitated solid is isolated; m.p. 138°-139° C. (from toluene).

Workup

  1. waitis boiled for a further 30 minutes
  2. temperatureto cool
  3. customThe precipitated solid is isolated by suction
  4. filtrationfiltering
  5. washwashed with acetone
  6. temperaturethe residue is heated in a water/acetone mixture (1:1)
  7. additionAfter the separated sulfur has been poured off
  8. temperatureto cool
  9. customthe precipitated solid is isolated

Sources & evidence

ORD record
ord-d16790c1377a4c428b0eea47a823bc70
Source dataset
uspto-grants-1981_04
Patent number
US04260775

Linked notes

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