Hydrochloric Acid → HCID 13576498, compound

HRID 638567Notes

Reaction equation

HRID 638567 reaction equation
[CH3:1][O:2][C:3]1[CH:18]=[CH:17][C:6]([C:7]([C:9]2[N:13]=[C:12]([CH2:14][C:15]#N)[O:11][N:10]=2)=[O:8])=[CH:5][CH:4]=1.Cl.[OH2:20].[CH:21]([OH:24])([CH3:23])[CH3:22]>>[CH:21]([O:24][C:15](=[O:20])[CH2:14][C:12]1[O:11][N:10]=[C:9]([C:7](=[O:8])[C:6]2[CH:17]=[CH:18][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)[N:13]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 3776IsopropanolHCID 13576492HCID 13576492, compound

Product 1

HCID 13576498HCID 13576498, compound

Procedure

A mixture of [3-(4-methoxybenzoyl)-1,2,4-oxadiazol-5-yl]acetonitrile (39 g) in dry isopropanol (1 liter) was saturated with HCl gas. The resulting solution was refluxed for 5 hours, cooled, and poured into cold water (2 liters) with stirring. The aqueous mixture was extracted with Et2O (3×800 ml). The organics were washed with water (4×1 liter) until neutral and saturated NaCl, dried over Na2SO4, and concentrated in vacuo to give 59 g of an oil. The ester crystallized on standing and the supernatant oil was decanted away. The crystals (40 g) were purified by high pressure liquid chromatography (1.5% ethyl acetate/CH2Cl2) to yield 36 g (73%) of an oil which crystallized, m.p. 63°-64°.

Workup

  1. temperatureThe resulting solution was refluxed for 5 hours
  2. temperaturecooled
  3. extractionThe aqueous mixture was extracted with Et2O (3×800 ml)
  4. washThe organics were washed with water (4×1 liter) until neutral and saturated NaCl
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-f4cacbc1fae842c681ff34ed3263cb2e
Source dataset
uspto-grants-1985_12
Patent number
US04562186

Reaction notes

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