Hydrochloric Acid → 3-(5-Amino-2,3-dichlorophenylmethyl)-1-methyl-6-trifluoromethyluracil

HRID 274849Notes

Reaction equation

HRID 274849 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[CH:6][C:5]([N+:9]([O-])=O)=[CH:4][C:3]=1[CH2:12][N:13]1[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]1=[O:25].Cl>C(O)C.O.[Fe]>[NH2:9][C:5]1[CH:6]=[C:7]([Cl:8])[C:2]([Cl:1])=[C:3]([CH2:12][N:13]2[C:18](=[O:19])[CH:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[N:15]([CH3:24])[C:14]2=[O:25])[CH:4]=1

Participants

6

Reactant 2

HCID 313Hydrochloric AcidHCID 214781273-(2,3-Dichloro-5-nitrophenylmethyl)-1-methyl-6-trifluoromethyluracil

Product 1

HCID 214781223-(5-Amino-2,3-dichlorophenylmethyl)-1-methyl-6-trifluoromethyluracilYield 23.2%

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Conditions

Temperature
65 °C

Procedure

In flask were placed 7.47 grams (0.019 mole) of 3-(2,3-dichloro-5-nitrophenylmethyl)- 1 -methyl-6-trifluoromethyluracil and 5.68 grams (0.94 mole) of powdered iron in 115 mL of ethanol and 9 mL of water. Dropwise, 9.0 mL of concentrated hydrochloric acid was added to the reaction mixture. Upon completion of addition, the reaction mixture was heated to 65° C. and maintained at this temperature for three hours. After being cooled to ambient conditions, the reaction mixture was filtered through Celite filter aid, and the collected precipitate was washed several times with ethanol. The solid removed by filtration was then dissolved in ethyl acetate, and this solution was washed twice with a saturated aqueous solution of sodium chloride. The dark brown solution was dried over anhydrous sodium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving 1.62 grams of 3-(5-amino-2,3-dichlorophenylmethyl)-1-methyl-6-trifluoromethyluracil as a solid. This reaction was repeated.

Workup

  1. customIn flask were placed
  2. additionUpon completion of addition
  3. temperaturemaintained at this temperature for three hours
  4. temperatureAfter being cooled to ambient conditions
  5. filtrationthe reaction mixture was filtered through Celite
  6. filtrationfilter aid
  7. washthe collected precipitate was washed several times with ethanol
  8. customThe solid removed by filtration
  9. dissolutionwas then dissolved in ethyl acetate
  10. washthis solution was washed twice with a saturated aqueous solution of sodium chloride
  11. dry with materialThe dark brown solution was dried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customThe solvent was evaporated from the filtrate under reduced pressure

Sources & evidence

ORD record
ord-7bd46c6271ff4a91b936b8ade03c80da
Source dataset
uspto-grants-1995_02
Patent number
US05391541

Reaction notes

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