Hydrochloric Acid → 3-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 380800Notes

Reaction equation

HRID 380800 reaction equation
[Cl:1][C:2]1[CH:11]=[C:10]([F:12])[C:9]([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:8][C:3]=1[NH:4]C(=O)C.Cl>C(O)C.O1CCCC1>[NH2:4][C:3]1[C:2]([Cl:1])=[CH:11][C:10]([F:12])=[C:9]([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:8]=1

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 183659043-(5-acetylamino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 186192573-(5-amino-4-chloro-2-fluorophenyl)-1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 2′-chloro-5′-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4′-fluoroacetanilide (24.42 g, 64.3 mmol) in ethanol is treated with 2N hydrochloric acid (200 ml), diluted with tetrahydrofuran, refluxed overnight, cooled to room temperature, partially concentrated in vacuo to remove ethanol and tetrahydrofuran, neutralized with 3N sodium hydroxide solution, and extracted with ethyl acetate. The organic extracts are combined, washed sequentially with saturated sodium hydrogen carbonate solution and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to give the title product as a light, brown solid (20.3 g, mp 132-135° C.).

Workup

  1. temperaturerefluxed overnight
  2. concentrationpartially concentrated in vacuo
  3. customto remove ethanol and tetrahydrofuran
  4. extractionextracted with ethyl acetate
  5. washwashed sequentially with saturated sodium hydrogen carbonate solution and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-25f1f2934a2e4b7085f227a3ef6e69cb
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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