Water → HCID 19815309, compound

HRID 847090Notes

Reaction equation

HRID 847090 reaction equation
C([O:8][C:9]1[CH:26]=[CH:25][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]2[S:21][CH2:22][CH2:23][CH3:24])=[CH:11][CH:10]=1)C1C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>FC(F)(F)C(O)=O>[OH:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:13][N:14]2[C:18]([CH2:19][OH:20])=[CH:17][N:16]=[C:15]2[S:21][CH2:22][CH2:23][CH3:24])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 962WaterHCID 516892Sodium BicarbonateHCID 19815367HCID 19815367, compound

Product 1

HCID 19815309HCID 19815309, compoundYield 26.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of 1.40 g of 1-(4-benzyloxybenzyl)-2-propylthio-5-hydroxymethylimidazole in 15 mL of trifluoroacetic acid was refluxed for 0.25 hour. After cooling, the reaction was poured into water containing an excess of sodium bicarbonate, and the resulting emulsion was extracted with ethyl acetate. The combined organic phases were washed with brine, dried over anhydrous sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-5% methanol/chloroform) afforded 0.28 g of 1-(4-hydroxybenzyl)-2-propylthio-5-hydroxymethylimidazole; NMR (200 MHz, DMSO-d6): δ9.41 (s, 1h); 6.88 (s, 1h); 6.79 (A2B2, 4H); 5.14 (t, 1h); 5.07 (s, 2H); 4.33 (d, 2H); 2.89 (t, 2H); 1.54 (sext., 2H); 0.88 (t, 3H).

Workup

  1. temperatureAfter cooling
  2. extractionthe resulting emulsion was extracted with ethyl acetate
  3. washThe combined organic phases were washed with brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-841d5cf3aa4141dbbc479ede8c3bf0bb
Source dataset
uspto-grants-1992_08
Patent number
US05138069

Reaction notes

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