Triethylamine → 3-Phenyl-4-(methoxycarbonylmethylmercapto)-1,2,5-oxadiazole-2-oxide

HRID 274420Notes

Reaction equation

HRID 274420 reaction equation
[C:1]1([C:7]2[C:11]([N+]([O-])=O)=[N:10][O:9][N+:8]=2[O-:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:16]([O:20][CH3:21])(=[O:19])[CH2:17][SH:18].C(N(CC)CC)C>CO>[C:1]1([C:7]2[C:11]([S:18][CH2:17][C:16]([O:20][CH3:21])=[O:19])=[N:10][O:9][N+:8]=2[O-:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 16907Methyl ThioglycolateHCID 5606744-Nitro-3-phenylfuroxan

Product 1

HCID 109674373-Phenyl-4-(methoxycarbonylmethylmercapto)-1,2,5-oxadiazole-2-oxide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 4.6 g of 3-phenyl-4-nitrofuroxan, 2.4 g of methyl thioglycolate and 2.2 g of triethylamine in 50 ml of methanol is stirred under a nitrogen atmosphere. In the course of this, the mixture warms to about 40° C. After 1 hour, it is poured into ice-water, whereupon a solid separates after stirring briefly, which is filtered off with suction and recrystallised from isopropanol.

Workup

  1. customwarms to about 40° C
  2. stirringafter stirring briefly
  3. filtrationwhich is filtered off with suction
  4. customrecrystallised from isopropanol

Sources & evidence

ORD record
ord-3bd9d9a73d3248aca6167b9cf465312e
Source dataset
uspto-grants-1995_02
Patent number
US05389655

Reaction notes

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