Hydrochloric Acid → HCID 68621578, compound

HRID 78514Notes

Reaction equation

HRID 78514 reaction equation
[CH3:1][C:2](=[O:7])[CH2:3][C:4](=O)[CH3:5].[O:8]1[CH2:12][CH2:11][CH2:10][C@@H:9]1[CH2:13][NH:14][C:15]([NH2:17])=[S:16].CS(C)=O.Cl>O1CCCC1.C(OCC)(=O)C>[NH:17]=[C:15]1[N:14]([CH2:13][C@H:9]2[CH2:10][CH2:11][CH2:12][O:8]2)[C:4]([CH3:5])=[C:3]([C:2](=[O:7])[CH3:1])[S:16]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 31261AcetylacetoneHCID 1810731{[(2R)-oxolan-2-yl]methyl}thiourea

Product 1

HCID 68621578HCID 68621578, compound

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of pentane-2,4-dione (451 mg, 4.5 mmol) and the product from Example 278A (786 mg, 4.5 mmol) in tetrahydrofuran (5 mL) was added a mixture of dimethylsulfoxide (0.64 mL, 9.0 mmol) and concentrated HCl (0.75 mL, 9.0 mmol). The reaction mixture was heated at 40° C. for 12 hours. After cooling to ambient temperature, the mixture was diluted with ethyl acetate and washed with saturated aqueous NaHCO3. The organic extract was dried (Na2SO4), filtered and concentrated to afford the title compound. MS (ESI) m/z 241 (M+H)+.

Workup

  1. temperatureAfter cooling to ambient temperature
  2. washwashed with saturated aqueous NaHCO3
  3. extractionThe organic extract
  4. dry with materialwas dried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b5551c527bd6407b8438ed12bf3f8131
Source dataset
uspto-grants-2014_09
Patent number
US08841334B2

Reaction notes

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