Cyclopropanemethanol → HCID 13519411, compound

HRID 370711Notes

Reaction equation

HRID 370711 reaction equation
[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H][H].[C:8]([N:10]1[CH2:15][CH2:14][CH:13]([C:16]2[C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=3[S:18][N:17]=2)[CH2:12][CH2:11]1)#[N:9]>>[CH:1]1([CH2:4][O:5][C:8]([N:10]2[CH2:15][CH2:14][CH:13]([C:16]3[C:20]4[CH:21]=[CH:22][CH:23]=[CH:24][C:19]=4[S:18][N:17]=3)[CH2:12][CH2:11]2)=[NH:9])[CH2:3][CH2:2]1

Participants

4

Reactant 3

HCID 75644CyclopropanemethanolHCID 13324092HCID 13324092, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 13519411HCID 13519411, compound

Conditions

Temperature
60 °C

Procedure

To 15 ml of cyclopropylcarbinol was added 0.05 g of Na metal. After the evolution of hydrogen gas ceased, 3-(1-cyano-4-piperidinyl)-1,2-benzisothiazole (4.0 g, 0.016 mole) was added. The temperature was raised to 60° C. to obtain a solution. Heat was removed and the reaction mixture was stirred at ambient temperature for 16 hours. Dry ice was added to the reaction mixture to destroy the excess alkoxide and the mixture was poured into water. The aqueous mixture was extracted with EtOAc. The EtOAc extract was washed with water and dried over MgSO4, and the solvent was removed in vacuo to leave an oil. The oil was triturated with hexane to yield 4.0 g of a solid. The solid was recrystallized twice from isopropyl ether to yield 2.4 g (46.3%) of the imidate as a solid, m.p. 85°-87°.

Workup

  1. customto obtain a solution
  2. temperatureHeat
  3. customwas removed
  4. additionDry ice was added to the reaction mixture
  5. customto destroy the excess alkoxide
  6. additionthe mixture was poured into water
  7. extractionThe aqueous mixture was extracted with EtOAc
  8. extractionThe EtOAc extract
  9. washwas washed with water
  10. dry with materialdried over MgSO4
  11. customthe solvent was removed in vacuo
  12. customto leave an oil
  13. customThe oil was triturated with hexane

Sources & evidence

ORD record
ord-224ab392fb79482f87ed89e3815dfeb5
Source dataset
uspto-grants-1985_07
Patent number
US04528292

Reaction notes

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