2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → Ethyl 5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

HRID 1274586

Reaction equation

HRID 1274586 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:16]=1.CN(C)[C:19]1[O:20][C:21](=[O:29])[CH:22]=[C:23]([C:25]([F:28])([F:27])[F:26])[N:24]=1>C(O)(=O)C>[O:20]=[C:19]1[NH:24][C:23]([C:25]([F:26])([F:27])[F:28])=[CH:22][C:21](=[O:29])[N:1]1[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([CH2:10][C:11]([O:13][CH2:14][CH3:15])=[O:12])[C:6]=2[CH:16]=1

Participants

4

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 11770464Ethyl 5-amino-1,2-benzisothiazole-3-acetate

Product 1

HCID 10960337Ethyl 5-[3,6-dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetate

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 5-amino-1,2-benzisothiazole-3-acetate (0.748 g, 3.16 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (0.660 g, 3.17 mmol) in acetic acid is refluxed for three hours, concentrated in vacuo, and diluted with saturated sodium hydrogen carbonate solution. The resultant mixture is extracted with methylene chloride. The combined organic extracts are washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to give the title product as a tan solid which is identified by NMR spectral analysis.

Workup

  1. temperatureis refluxed for three hours
  2. concentrationconcentrated in vacuo
  3. additiondiluted with saturated sodium hydrogen carbonate solution
  4. extractionThe resultant mixture is extracted with methylene chloride
  5. washThe combined organic extracts are washed with water
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c9d55bb43744ba9a82ea4d0a2030068
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Linked notes

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