Hydrochloric Acid → HCID 15676104, compound

HRID 1646572Notes

Reaction equation

HRID 1646572 reaction equation
[Na].[CH3:2][N:3]([CH3:25])[C:4]1[N:8]=[C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17](=[O:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[CH3:10])[O:6][N:5]=1.Cl>CO>[CH3:25][N:3]([CH3:2])[C:4]1[N:8]=[C:7]([CH:9]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([CH:17]([OH:24])[C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[CH:12]=2)[CH3:10])[O:6][N:5]=1

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 15676082HCID 15676082, compound

Product 1

HCID 15676104HCID 15676104, compoundYield 103.1%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To sodium brohydride suspended (0.177 g, 4.7 mmol) in methanol (15 ml) under cooling with ice was slowly added dropwise 3-dimethylamino-5-(1-(3-benzoylphenyl) ethyl)-1,2,4-oxadiazole (1.45 g, 4.5 mmol) in methanol (15 ml). After the mixture was stirred under cooling with ice with 1 h, 1N-HCl was added to the mixture, then the mixture was adjusted at pH 6. The mixture was evaporated under reduced pressure to a residue, which was extracted with dichloromethane. The extracts were washed with saturated NaCl aq., dried with anhydrous magnesium sulfate, and evaporated under reduced pressure to a residue, which was chlomatographed to afford 3-dimethylamino-5-(1-(3-(α-hydroxybenzyl)phenyl)ethyl)- 1,2,4-oxadiazole (1.50 g, 99% yield) as oily substance: NMR(CDCl3)δ1.45(d, 3H), 2.27(d, 1H), 3.00(s, 6H), 4.20(q, 1H), 5.80(d, 1H), 7.20-7.45 m(m, 9H) ppm; IR(neat) 3375, 1600, 1405 cm-1.

Workup

  1. temperatureunder cooling with ice
  2. temperatureunder cooling with ice with 1 h
  3. customThe mixture was evaporated under reduced pressure to a residue, which
  4. extractionwas extracted with dichloromethane
  5. washThe extracts were washed with saturated NaCl aq.
  6. dry with materialdried with anhydrous magnesium sulfate
  7. customevaporated under reduced pressure to a residue, which

Sources & evidence

ORD record
ord-1e12219464214cc5a250fb4dbf678b11
Source dataset
uspto-grants-1993_01
Patent number
US05180731

Reaction notes

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