Formic Acid → 2-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propane-1,2-diol

HRID 2232266Notes

Reaction equation

HRID 2232266 reaction equation
[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]1([CH2:12][N:13]2[CH:17]=[N:16][CH:15]=[N:14]2)[CH2:11][O:10]1.C(O)=[O:19]>>[F:1][C:2]1[CH:7]=[C:6]([F:8])[CH:5]=[CH:4][C:3]=1[C:9]([OH:19])([CH2:12][N:13]1[CH:17]=[N:16][CH:15]=[N:14]1)[CH2:11][OH:10]

Participants

3

Reactant 2

HCID 284Formic AcidHCID 101309211-(2-(2,4-Difluorophenyl)-2,3-epoxypropyl)-1H-1,2,4-triazole

Product 1

HCID 109888402-(2,4-Difluorophenyl)-3-(1H-1,2,4-triazol-1-yl)propane-1,2-diol

Procedure

Heat a solution of 1-[[2-(2,4-difluorophenyl)oxiranyl]methyl]-1H-1,2,4-triazole (57 g) [prepared as described in Example 2(c) of British patent application No. 2,099,818A, published 15 Dec. 1982] in formic acid (500 mL) at reflux overnight. Remove the solvent in vacuo at 85°. Dilute the residue with ice water (1 liter) and basify carefully with 10% K2CO3 solution. Dilute with MeOH (500 mL) and heat on steam bath (1.5hr). Remove the MeOH in vacuo and extract the remaining aqueous solution with EtOAc (2×500 mL). Wash the EtOAc layer with H2O and dry it oyer MgSO4 and evaporate it to dryness to give 49.7 g of the title compound as a solid, m.p. 130°-132° C.

Workup

  1. customprepared
  2. customRemove the solvent in vacuo at 85°
  3. additionDilute the residue with ice water (1 liter)
  4. additionDilute with MeOH (500 mL)
  5. temperatureheat on steam bath (1.5hr)
  6. customRemove the MeOH in vacuo
  7. extractionextract the remaining aqueous solution with EtOAc (2×500 mL)
  8. washWash the EtOAc layer with H2O
  9. dry with materialdry it oyer MgSO4
  10. customevaporate it to dryness

Sources & evidence

ORD record
ord-be4791a4d5ad42989646316129847bde
Source dataset
uspto-grants-1988_11
Patent number
US04788190

Reaction notes

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