Hydrochloric Acid → Tiafenacil

HRID 215912Notes

Reaction equation

HRID 215912 reaction equation
[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][NH:6][C:7](=[O:11])[CH:8](Cl)[CH3:9].C(=O)([O-])[O-].[K+].[K+].[Cl:19][C:20]1[C:25]([SH:26])=[CH:24][C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:37])([F:36])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])=[C:22]([F:40])[CH:21]=1.Cl>C(#N)C.C(OCC)(=O)C.O>[CH3:1][O:2][C:3](=[O:12])[CH2:4][CH2:5][NH:6][C:7](=[O:11])[CH:8]([S:26][C:25]1[CH:24]=[C:23]([N:27]2[C:32](=[O:33])[CH:31]=[C:30]([C:34]([F:36])([F:37])[F:35])[N:29]([CH3:38])[C:28]2=[O:39])[C:22]([F:40])=[CH:21][C:20]=1[Cl:19])[CH3:9]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 186192703-(4-Chloro-2-fluoro-5-sulfanylphenyl)-1-methyl-6-(trifluoromethyl)-1,2,3,4-tetrahydropyrimidine-2,4-dioneHCID 43665913Methyl 3-(2-Chloropropanamido)propanoate

Product 1

HCID 67295585TiafenacilYield 78%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6342AcetonitrileSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of 3-(2-chloropropionylamino)propionic acid methyl ester (6.93 g) and potassium carbonate (4.72 g) in acetonitrile (150 mL) was added dropwise a solution of 3-(4-chloro-2-fluoro-5-mercaptophenyl)-1-methyl-6-trifluoromethyl-1H-pyrimidin-2,4-dione (11.54 g) in acetonitrile (75 mL) at 45° C. to 50° C. for 1 hour. The reaction mixture was stirred at the same temperature for 2 hours and neutralized at 5° C. with 1 N hydrochloric acid. Water and ethyl acetate were added to separate the organic layer. The aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with brine, dried with magnesium sulfate, filtered, concentrated, and recrystallized with ether to give the target compound (13.00 g, yield 78%, white solid).

Workup

  1. customto separate the organic layer
  2. extractionThe aqueous layer was extracted with ethyl acetate
  3. washThe combined organic layer was washed with brine
  4. dry with materialdried with magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customrecrystallized with ether
  8. customto give the target compound (13.00 g, yield 78%, white solid)

Sources & evidence

ORD record
ord-33638db1f95240b6a6e6be9441775615
Source dataset
uspto-grants-2012_06
Patent number
US08193198B2

Reaction notes

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