Acetic Acid → 3-[3-(6-Methoxy-m-tolyl)-1,2-benzisoxazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 277358Notes

Reaction equation

HRID 277358 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[O:9][N:8]=[C:7]([C:10]3[CH:11]=[C:12]([CH3:18])[C:13]([O:16][CH3:17])=[CH:14][CH:15]=3)[C:6]=2[CH:19]=1.CN(C)[C:22]1[O:23][C:24](=[O:32])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[N:27]=1.C(O)(=O)C>O>[CH3:17][O:16][C:13]1[C:12]([CH3:18])=[CH:11][C:10]([C:7]2[C:6]3[CH:19]=[C:2]([N:1]4[C:24](=[O:32])[CH:25]=[C:26]([C:28]([F:31])([F:30])[F:29])[NH:27][C:22]4=[O:23])[CH:3]=[CH:4][C:5]=3[O:9][N:8]=2)=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 698321145-Amino-3-(6-methoxy-m-tolyl)-1,2-benzisoxazole

Product 1

HCID 700979223-[3-(6-Methoxy-m-tolyl)-1,2-benzisoxazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 5-amino-3-(6-methoxy-m-tolyl)-1,2-benzisoxazole (8.40 g, 0.033 mol), 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (7.60 g, 0.036 mol), and acetic acid is refluxed for three hours, cooled, poured onto ice, and diluted with water. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and dried to give the title product as a pink solid which is identified by NMR spectral analyses.

Workup

  1. temperatureis refluxed for three hours
  2. temperaturecooled
  3. additionpoured onto ice
  4. filtrationThe resultant aqueous mixture is filtered
  5. customto obtain a solid
  6. washThe solid is washed with water
  7. customdried

Sources & evidence

ORD record
ord-77fc3eeb456840d38d7b912f11ee3ca4
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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