Hydrochloric Acid → 2-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzaldehyde

HRID 566602Notes

Reaction equation

HRID 566602 reaction equation
[CH2:1]=[O:2].Cl.CON=C[C:8]1[CH:13]=[C:12]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:24])([F:23])[F:22])[N:16]([CH3:25])[C:15]2=[O:26])[C:11]([F:27])=[CH:10][C:9]=1[Cl:28].O>C(O)(=O)C>[Cl:28][C:9]1[CH:10]=[C:11]([F:27])[C:12]([N:14]2[C:19](=[O:20])[CH:18]=[C:17]([C:21]([F:22])([F:24])[F:23])[N:16]([CH3:25])[C:15]2=[O:26])=[CH:13][C:8]=1[CH:1]=[O:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 712FormaldehydeHCID 962WaterHCID 538363112-Chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime

Product 1

HCID 212012522-Chloro-4-fluoro-5-[3-methyl-2,6-dioxo-4-(trifluoromethyl)pyrimidin-1-yl]benzaldehyde

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

150 ml of a 30% by weight aqueous formaldehyde solution and 150 35 ml of concentrated hydrochloric acid were added dropwise to a solution of 189.9 g (0.50 mol) of 2-chloro-4-fluoro-5-(1-methyl-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedion-3-yl)benzaldehyde (O-methyl)oxime in 0.75 l of glacial acetic acid. The mixture was subsequently refluxed for two hours. After cooling, 0.75 l of water were added, whereupon the solid product of value formed was separated off and washed first with water until the reaction was neutral and then with petroleum ether. Yield: 140 g;

Workup

  1. temperatureThe mixture was subsequently refluxed for two hours
  2. temperatureAfter cooling
  3. customformed
  4. customwas separated off
  5. washwashed first with water until the reaction

Sources & evidence

ORD record
ord-248f42b26eab416d81db2b50f2ab5bf8
Source dataset
uspto-grants-2001_01
Patent number
US06175007B1

Reaction notes

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