Ethyl orthoformate → HCID 135760588, compound

HRID 2372729Notes

Reaction equation

HRID 2372729 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-7c2c7b04205d46b99839090ae7e78b6f
Source dataset
uspto-grants-1992_03
Patent number
US05100893

Reaction notes

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