Hydrochloric Acid → 3-(3-hydroxymethyl-phenyl)-4H-[1,2,4]oxadiazol-5-one

HRID 1161112Notes

Reaction equation

HRID 1161112 reaction equation
Cl.O1CCCCC1[O:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1>O1CCCC1.[Cl-].[Na+].O>[OH:8][CH2:9][C:10]1[CH:11]=[C:12]([C:16]2[NH:20][C:19](=[O:21])[O:18][N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 1363488113-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-one

Product 1

HCID 1360829183-(3-hydroxymethyl-phenyl)-4H-[1,2,4]oxadiazol-5-oneYield 99%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

Add 10% hydrochloric acid (100 ml) to a solution of 3-[3-(tetrahydro-pyran-2-yloxymethyl)-phenyl]-4H-[1,2,4]oxadiazol-5-one (4.50 g, 16.3 mmol) in tetrahydrofuran (0.1M) and stir. After 18 hours, pour reaction into brine and extract with ethyl acetate. Combine the organic layers, dry with sodium sulfate, filter and concentrate under reduced pressure to yield the title product as a white solid (3.10 g, 99%): 1H NMR (DMSO-d6) δ 4.57 (s, 2H), 7.55 (m, 2H), 7.67 (dt, 1H), 7.81 (m, 1H), 12.95 (bs, 1H).

Workup

  1. additionpour
  2. extractionextract with ethyl acetate
  3. dry with materialdry with sodium sulfate
  4. filtrationfilter
  5. concentrationconcentrate under reduced pressure

Sources & evidence

ORD record
ord-970a43ed42224c14a97dfa9effb062df
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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