5-Amino-3-(1-methylpyrrol-2-yl)-1,2-benzisothiazole → 3-[3-(1-Methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

HRID 48962Notes

Reaction equation

HRID 48962 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([C:10]3[N:11]([CH3:15])[CH:12]=[CH:13][CH:14]=3)[C:6]=2[CH:16]=1.CN(C)[CH:19]1[N:24]=[C:23]([C:25]([F:28])([F:27])[F:26])[CH2:22][C:21](=[O:29])[O:20]1>C(O)(=O)C>[CH3:15][N:11]1[CH:12]=[CH:13][CH:14]=[C:10]1[C:7]1[C:6]2[CH:16]=[C:2]([N:1]3[C:21](=[O:29])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[NH:24][C:19]3=[O:20])[CH:3]=[CH:4][C:5]=2[S:9][N:8]=1

Participants

4

Reactant 2

HCID 206342755-Amino-3-(1-methylpyrrol-2-yl)-1,2-benzisothiazoleHCID 69891695HCID 69891695, compound

Product 1

HCID 206342623-[3-(1-Methylpyrrol-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracilYield 83.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 5-amino-3-(1-methylpyrrol-2-yl)-1,2-benzisothiazole(1.05 g, 4.59 mmol) and acetic acid is added 2-(dimethylamino)-4-(trifluoromethyl)-5H-1,3-oxazin-6-one (0.960 g, 4.60 mmol). The resultant mixture is stirred at reflux for two hours, cooled to room temperature, diluted with ice water and stirred vigorously for approximately 15 minutes. Filtration and drying affords the title compound as a gray solid (1.50 g, 83.3%, mp 125-130° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux for two hours
  2. filtrationFiltration
  3. customdrying

Sources & evidence

ORD record
ord-d937514b0b2040f180fa853fa0acbf8c
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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