Ethanol → HCID 178470470, compound

HRID 614235Notes

Reaction equation

HRID 614235 reaction equation
[CH3:1][O:2][C:3]1[CH:12]=[CH:11][C:6]([CH2:7][N:8]=[C:9]=[S:10])=[CH:5][CH:4]=1.[C:13]([NH:18][NH2:19])(=O)[C:14]([OH:16])=[O:15].[CH2:20](O)[CH3:21]>>[CH2:20]([O:16][C:14]([C:13]1[N:8]([CH2:7][C:6]2[CH:11]=[CH:12][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[C:9]([SH:10])=[N:19][N:18]=1)=[O:15])[CH3:21]

Participants

4

Reactant 3

HCID 702EthanolHCID 1231974-Methoxybenzyl isothiocyanateHCID 222877Hydrazino(oxo)acetic acid

Product 1

HCID 178470470HCID 178470470, compound

Procedure

A solution of p-methoxybenzyl isothiocyanate (8.95 g.) and the ethyl ester of oxalic acid monohydrazide (6.8 g.) in ethanol (50 ml.) was refluxed for a period of approximately 16 hours (overnight). The hot solution was then filtered, the filtrate evaporated in vacuo and the resulting oil triturated with dry diethyl ester. The solid product so obtained, viz., 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water to yield 4.0 g. of pure material. The analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.).

Workup

  1. filtrationThe hot solution was then filtered
  2. customthe filtrate evaporated in vacuo
  3. customthe resulting oil triturated with dry diethyl ester
  4. customThe solid product so obtained
  5. custom, 3-ethoxycarbonyl-4-(p-methoxybenzyl)-1,2,4-triazole-5-thiol (yield, 7.2 g.) was then recrystallized from ethanol-water
  6. customto yield 4.0 g
  7. customThe analytical sample melted at 142°-144° C. after a further recrystallization from ethyl acetate/petroleum ether (b.p. 60°-80° C.)

Sources & evidence

ORD record
ord-f9443c25886e4d3686275e635d49d858
Source dataset
uspto-grants-1979_03
Patent number
US04144240

Reaction notes

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