Methyl chloroacetate → HCID 20475380, compound

HRID 443589Notes

Reaction equation

HRID 443589 reaction equation
Cl[CH2:2][C:3]([O:5][CH3:6])=[O:4].[CH2:7]([NH:11][C:12](=S)[NH:13][NH2:14])[CH:8]([CH3:10])[CH3:9].O1CC[CH2:18][CH2:17]1>>[CH2:7]([NH:11][C:12]1[C:2]([C:3]([O:5][CH3:6])=[O:4])=[C:17]([CH3:18])[NH:14][N:13]=1)[CH:8]([CH3:10])[CH3:9]

Participants

4

Reactant 3

HCID 7295Methyl chloroacetateHCID 8028TetrahydrofuranHCID 12367441HCID 12367441, compound

Product 1

HCID 20475380HCID 20475380, compound

Procedure

15.1 g of methyl 2-chloroacetate is added to a suspension of 14.7 g of 4-isobutylthiosemicarbazide in 150 ml of tetrahydrofuran. The mixture is stirred for 30 minutes and then boiled. After stirring for a further hour at 65° C., the mixture is cooled, the precipitated solid is isolated and washed with acetone. The residue is dissolved hot in water, filtered off from the precipitated sulfur and, after cooling, aqueous ammonia solution is added. After suction filtering and drying the product, 3-isobutylamino-4-methoxycarbonyl-5-methylpyrazole is isolated; m.p. 100°-103° C.

Workup

  1. stirringAfter stirring for a further hour at 65° C.
  2. temperaturethe mixture is cooled
  3. customthe precipitated solid is isolated
  4. washwashed with acetone
  5. dissolutionThe residue is dissolved hot in water
  6. filtrationfiltered off from the precipitated sulfur
  7. temperatureafter cooling
  8. additionaqueous ammonia solution is added
  9. filtrationAfter suction filtering
  10. customdrying the product

Sources & evidence

ORD record
ord-b57116b2ced749d1999161d3c95a656d
Source dataset
uspto-grants-1981_04
Patent number
US04260775

Reaction notes

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