Water → HCID 14835400, compound

HRID 1199023Notes

Reaction equation

HRID 1199023 reaction equation
[C:1]1([C:7]2[O:8][N:9]=[C:10]3[C:15]([CH2:16][C:17]#[N:18])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[OH-:19].[K+].O>C(O)(C)(C)C>[C:1]1([C:7]2[O:8][N:9]=[C:10]3[C:15]([CH2:16][C:17]([NH2:18])=[O:19])=[CH:14][CH:13]=[CH:12][C:11]=23)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 14797Potassium HydroxideHCID 15634757HCID 15634757, compound

Product 1

HCID 14835400HCID 14835400, compoundYield 12%

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

A slurry of 4.0 g (0.017 mole) of 3-phenyl-2,1-benzisoxazol-7-acetonitrile in 175 ml of t-butanol was heated to reflux and treated with 5 g (0.09 mole) of powdered potassium hydroxide. The deep blue colored reaction mixture was heated at reflux for 0.5 hr, cooled and poured into 800 ml of water. The mixture was extracted with three 100 ml portions of methylene chloride. The combined extracts were washed with water, dried over sodium sulfate, and concentrated to give a brown solid as residue. The solid was recrystallized from 2-propanol (charcoal) and then subjected to vacuum sublimation at 160°-170° C. to yield 0.5 g (12%) of an off-white powder, m.p. 191°-192° C. after recrystallization from absolute ethyl alcohol.

Workup

  1. temperatureto reflux
  2. temperatureThe deep blue colored reaction mixture was heated
  3. temperatureat reflux for 0.5 hr
  4. temperaturecooled
  5. extractionThe mixture was extracted with three 100 ml portions of methylene chloride
  6. washThe combined extracts were washed with water
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto give a brown solid as residue
  10. customThe solid was recrystallized from 2-propanol (charcoal)
  11. customsubjected to vacuum sublimation at 160°-170° C.

Sources & evidence

ORD record
ord-add884475a384563973cdf76cd3315b4
Source dataset
uspto-grants-1990_02
Patent number
US04898874

Reaction notes

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