Ethyl orthoformate → HCID 135760588, compound

HRID 1614324Notes

Reaction equation

HRID 1614324 reaction equation
[OH:1][NH:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=1)=[NH:4].[CH2:12](OC(OCC)OCC)C>O>[O:1]1[CH:12]=[N:4][C:3]([C:5]2[CH:10]=[CH:9][C:8]([OH:11])=[CH:7][CH:6]=2)=[N:2]1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 51497564,N-Dihydroxy-benzamidine

Product 1

HCID 135760588HCID 135760588, compoundYield 23.1%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 6.2 parts of N,4-dihydroxybenzenecarboximidamide and 44.6 parts of triethoxymethane was stirred overnight at reflux temperature. The reaction mixture was poured into water and the product was extracted with trichloromethane. The extract was dried, filtered and evaporated. The residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 99:1). The eluent of the desired fraction was evaporated, yielding 1.5 parts (23.1%) of 4-(1,2,4-oxadiazol-3-yl)phenol (interm. 10).

Workup

  1. temperatureat reflux temperature
  2. extractionthe product was extracted with trichloromethane
  3. customThe extract was dried
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (silica gel; CHCl3 /CH3OH 99:1)
  7. customThe eluent of the desired fraction was evaporated

Sources & evidence

ORD record
ord-035a9526c2d545c19a036bcf9079d1dd
Source dataset
uspto-grants-1993_03
Patent number
US05196535

Reaction notes

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