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

HRID 1274545

Reaction equation

HRID 1274545 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[C:15]([O:16][CH3:17])=[CH:14][C:13]([CH3:18])=[C:12]([CH3:19])[CH:11]=3)[C:6]=2[CH:20]=1.CN(C)[C:23]1[O:24][C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[N:28]=1.C(O)(=O)C.O>C(Cl)Cl.C(OCC)C>[CH3:17][O:16][C:15]1[C:10]([C:7]2[C:6]3[CH:20]=[C:2]([N:1]4[C:25](=[O:33])[CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[NH:28][C:23]4=[O:24])[CH:3]=[CH:4][C:5]=3[S:9][N:8]=2)=[CH:11][C:12]([CH3:19])=[C:13]([CH3:18])[CH:14]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 183145035-Amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole

Product 1

HCID 154776123-[3-(6-Methoxy-3,4-xylyl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 62.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 5-amino-3-(6-methoxy-3,4-xylyl)-1,2-benzisothiazole (8.53 g, 30.0 mmol), 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (6.87 g, 33.0 mmol) and acetic acid is refluxed for 2 hours, cooled, and poured into water. The resultant aqueous mixture is filtered to obtain a solid. A solution of the solid in methylene chloride is washed sequentially with water and brine, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and a 5% diethyl ether in methylene chloride solution gives the title product as a yellow foam (8.37 g, 62.0%) which is identified by NMR spectral analyses.

Workup

  1. temperatureis refluxed for 2 hours
  2. temperaturecooled
  3. filtrationThe resultant aqueous mixture is filtered
  4. customto obtain a solid
  5. washA solution of the solid in methylene chloride is washed sequentially with water and brine
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customto obtain an oil

Sources & evidence

ORD record
ord-9d1e892e80704d99a6cb91d363b8005e
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Linked notes

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