Hydrochloric Acid → HCID 178487771, compound

HRID 1374671Notes

Reaction equation

HRID 1374671 reaction equation
C(C1NC=[CH:11][N:12]=1)(C1NC=CN=1)=O.CCCCCC.[C:19]([O:22][CH2:23][CH3:24])(=O)C.[OH2:25].Cl.[CH2:27]1[CH2:31][O:30][CH2:29][CH2:28]1>>[OH:25][C:11]1[C:27]2[CH:28]=[CH:29][C:23]([O:22][CH3:19])=[CH:24][C:31]=2[O:30][N:12]=1

Participants

6

Reactant 5

HCID 313Hydrochloric AcidHCID 962WaterHCID 8028Tetrahydrofuran2×HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 21226206Ethyl acetate hexane

Product 1

HCID 178487771HCID 178487771, compound

Procedure

A solution of carbonyl diimidazole (1.07 g, 6.57 mmol) in anhydrous THF (8 ml) was added to a stirred boiling solution of the hydroxamic acid (602 mg, 3.29 mmol) in THF (6 ml). The resulting solution was heated at reflux for approx. 8–10 hours, then allowed to cool to room temperature and stirred overnight under an argon atmosphere. Thin layer chromatography (tlc) (silica; 1:1 hexane/ethyl acetate) showed minimal starting material and new non polar material. The solution was evaporated on a rotary evaporator to give an orange coloured oil. Water (6 ml) was added, and contents cooled (ice bath) and acidified to pH 2 with concentrated hydrochloric acid. The crude, damp 3-hydroxy-6-methoxy-1,2-benzisoxazole precipitated as a cream orange solid (645 mg).

Workup

  1. temperatureThe resulting solution was heated
  2. temperatureat reflux for approx. 8–10 hours
  3. customThe solution was evaporated on a rotary evaporator
  4. customto give an orange coloured oil
  5. temperaturecontents cooled (ice bath)
  6. customThe crude, damp 3-hydroxy-6-methoxy-1,2-benzisoxazole precipitated as a cream orange solid (645 mg)

Sources & evidence

ORD record
ord-9c45cfb086fb4562a5141363750c265f
Source dataset
uspto-grants-2007_01
Patent number
US07166604B2

Reaction notes

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