Hydrochloric Acid → HCID 68621578, compound

HRID 1037936Notes

Reaction equation

HRID 1037936 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-5b88b39338b64edcb5c44d5eeb435516
Source dataset
uspto-grants-2013_10
Patent number
US08546583B2

Reaction notes

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