2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → 2'-chloro-5'-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4'-fluoroacetanilide

HRID 380798Notes

Reaction equation

HRID 380798 reaction equation
[NH2:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([Cl:12])=[C:6]([CH:11]=1)[NH:7][C:8](=[O:10])[CH3:9].CN(C)[C:16]1[O:17][C:18](=[O:26])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[N:21]=1>C(O)(=O)C.O>[Cl:12][C:5]1[CH:4]=[C:3]([F:13])[C:2]([N:1]2[C:18](=[O:26])[CH:19]=[C:20]([C:22]([F:25])([F:24])[F:23])[NH:21][C:16]2=[O:17])=[CH:11][C:6]=1[NH:7][C:8](=[O:10])[CH3:9]

Participants

5

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 183659355'-Amino-2'-chloro-4'-fluoroacetanilide

Product 1

HCID 183658882'-chloro-5'-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-4'-fluoroacetanilideYield 78.1%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A mixture of 5′ -amino-2′-chloro-4′-fluoroacetanilide (1.0 g, 4.9 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (1.0 g, 4.9 mmol) in acetic acid is refluxed for 90 minutes and diluted with water. The resultant aqueous mixture is filtered to obtain the title product as an off-white solid (1.4 g, mp 264-266° C.) which is identified by 1H, 13C and 9F NMR spectral analyses.

Workup

  1. temperatureis refluxed for 90 minutes
  2. filtrationThe resultant aqueous mixture is filtered

Sources & evidence

ORD record
ord-d40e96837be84ca38d8fe0b1526a4302
Source dataset
uspto-grants-2001_10
Patent number
US06303783B1

Reaction notes

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