Ethanol → HCID 178470470, compound

HRID 2052248Notes

Reaction equation

HRID 2052248 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-3feb0b11833f4aabb62e3b7150fdf252
Source dataset
uspto-grants-1980_01
Patent number
US04183925

Reaction notes

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