Isopropylamine → HCID 86744781, compound

HRID 2051288Notes

Reaction equation

HRID 2051288 reaction equation
Cl[CH2:2][C:3](=[N:17][OH:18])[CH2:4][O:5][C:6]1[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:9][S:8][N:7]=1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>C1COCC1>[CH:19]([NH:22][CH2:2][C:3](=[N:17][OH:18])[CH2:4][O:5][C:6]1[C:10]([N:11]2[CH2:16][CH2:15][O:14][CH2:13][CH2:12]2)=[N:9][S:8][N:7]=1)([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 73189422HCID 73189422, compound

Product 1

HCID 86744781HCID 86744781, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

In a 200 mL round-bottomed flask were placed 3-chloro-1-[(4-morpholino-1,2,5-thiadiazol-3-yl)oxy]-2-propanone oxime 4b (3.53 g, 12.1 mmole), isopropylamine (3.56 g, 60.3 mmole), and THF (71 mL). The mixture was stirred at room temperature for 2.5 hours. The reaction mixture was concentrated in vacuo at room temperature. The residue was triturated with isopropyl ether and precipitated crystals were filtered with suction. The crystals were dissolved in dil. HCl solution. To the solution were added ether and NaHCO3 in small portions under vigorous stirring conditions. The organic layer was washed with water and dried over anyydrous MgSO4, and concentrated in vacuo. Yield: 0.42 g (11.6%) from isopropyl ether.

Workup

  1. customIn a 200 mL round-bottomed flask were placed
  2. concentrationThe reaction mixture was concentrated in vacuo at room temperature
  3. customThe residue was triturated with isopropyl ether
  4. customprecipitated crystals
  5. filtrationwere filtered with suction
  6. dissolutionThe crystals were dissolved in dil. HCl solution
  7. additionTo the solution were added ether and NaHCO3 in small portions
  8. stirringunder vigorous stirring conditions
  9. washThe organic layer was washed with water
  10. dry with materialdried over anyydrous MgSO4
  11. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5992bd0a39d441a1ab02bce21389b7cf
Source dataset
uspto-grants-1991_05
Patent number
US05017618

Reaction notes

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