2-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one → {{5-[3,6-Dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrile

HRID 277389Notes

Reaction equation

HRID 277389 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]#[N:13])[C:6]=2[CH:14]=1.CN(C)[C:17]1[O:18][C:19](=[O:27])[CH:20]=[C:21]([C:23]([F:26])([F:25])[F:24])[N:22]=1>C(O)(=O)C>[O:18]=[C:17]1[NH:22][C:21]([C:23]([F:24])([F:25])[F:26])=[CH:20][C:19](=[O:27])[N:1]1[C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([O:10][CH2:11][C:12]#[N:13])[C:6]=2[CH:14]=1

Participants

4

Reactant 2

HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-oneHCID 18314508[(5-Amino-1,2-benzisothiazol-3-yl)oxy]acetonitrile

Product 1

HCID 15477614{{5-[3,6-Dihydro-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazol-3-yl}oxy}acetonitrileYield 34%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of [(5-amino-1,2-benzisothiazol-3-yl)oxy]-acetonitrile (4.30 g, 21.0 mmol) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (4.37 g, 21.0 mmol) in acetic acid is refluxed for three hours, stirred overnight at room temperature, and poured into an ice-water mixture. The resultant aqueous mixture is filtered to obtain a solid. The solid is washed with water and dried overnight in a vacuum oven at 55° C. to give the title product as a brown solid (2.63 g, mp 254-258° C.).

Workup

  1. temperatureis refluxed for three hours
  2. filtrationThe resultant aqueous mixture is filtered
  3. customto obtain a solid
  4. washThe solid is washed with water
  5. customdried overnight in a vacuum oven at 55° C.

Sources & evidence

ORD record
ord-8a18e959c4184e0e95e78be06530fc6f
Source dataset
uspto-grants-2002_03
Patent number
US06355796B1

Reaction notes

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