Hydrochloric Acid → HCID 18662967, compound

HRID 1956184Notes

Reaction equation

HRID 1956184 reaction equation
[CH3:1][C:2]([CH3:23])([CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:8]1[C:9]([S:14][CH3:15])=[N:10][CH:11]=[N:12][CH:13]=1)[C:3]([O:5]C)=[O:4].C[S-].[Na+].Cl>CN(C)C=O>[CH3:1][C:2]([CH3:23])([CH:7]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[F:22])[C:8]1[C:9]([S:14][CH3:15])=[N:10][CH:11]=[N:12][CH:13]=1)[C:3]([OH:5])=[O:4]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 4378561Sodium methanethiolateHCID 23227007HCID 23227007, compound

Product 1

HCID 18662967HCID 18662967, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 1.0 g (3.0 mmol) of methyl 2,2-dimethyl-3-(2-fluorophenyl)-3-(4-methylthio-5-pyrimidinyl)propanoate and 1.7 g (24 mmol) of sodium methanethiolate in 20 mL of dry N,N-dimethylformamide was heated to 50° C. with stirring for 30 minutes. The resulting solution was poured into dilute aqueous hydrochloric acid and the mixture obtained was extracted with ether. The ethereal extract was washed with water, dried over magnesium sulfate, filtered, and concentrated by evaporation under reduced pressure to obtain a light yellow solid. This solid was triturated in 30 mL of dichloromethane, collected by filtration, and dried under reduced pressure to obtain 570 mg (60 of theory) of the title compound as a light yellow solid melting at 204°-205° C.

Workup

  1. customthe mixture obtained
  2. extractionwas extracted with ether
  3. extractionThe ethereal extract
  4. washwas washed with water
  5. dry with materialdried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated by evaporation under reduced pressure
  8. customto obtain a light yellow solid
  9. customThis solid was triturated in 30 mL of dichloromethane
  10. filtrationcollected by filtration
  11. customdried under reduced pressure

Sources & evidence

ORD record
ord-860baadecaa34fccabef226aa7a5ae48
Source dataset
uspto-grants-1998_07
Patent number
US05780465

Reaction notes

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