Hydrochloric Acid → 3-[4-Cyano-3-methoxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

HRID 430919Notes

Reaction equation

HRID 430919 reaction equation
[CH3:1][O-:2].[Na+].[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[NH:14][C:13]2=[O:23])=[CH:8][C:7]=1[N+]([O-])=O)#[N:5].O.Cl>CO>[C:4]([C:6]1[CH:11]=[CH:10][C:9]([N:12]2[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[NH:14][C:13]2=[O:23])=[CH:8][C:7]=1[O:2][CH3:1])#[N:5]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 10942334Sodium MethoxideHCID 153346703-[4-Cyano-3-nitrophenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Product 1

HCID 187623443-[4-Cyano-3-methoxyphenyl]-6-trifluoromethyl-1,2,3,4-tetrahydropyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

Sodium methanolate solution (2.8 g of a 30 percent strength solution in methanol) was added to a solution of 3-[4-cyano-3-nitrophenyl]-6-trifluoromethyl-1,2,3,4-tetrahydro-pyrimidine-2,4-dione (2.4 g) in 50 ml of anhydrous methanol. The reaction mixture was subsequently refluxed for 5 hours. After cooling, water (50 ml) was added first, followed by 10% strength aqueous hydrochloric acid to a pH of 3-4. The precipitate formed was subsequently separated off, washed with water and petroleum ether and dried. Yield: 1.1 g; m.p.: >230° C.

Workup

  1. temperatureThe reaction mixture was subsequently refluxed for 5 hours
  2. temperatureAfter cooling
  3. customThe precipitate formed
  4. customwas subsequently separated off
  5. washwashed with water and petroleum ether
  6. customdried

Sources & evidence

ORD record
ord-a9eef262a9064dc5a0674e73245872b1
Source dataset
uspto-grants-2003_12
Patent number
US06656884B2

Reaction notes

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