1,2-Benzisothiazol-5-amine, 3-chloro- → 3-(3-chloro-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

HRID 48981Notes

Reaction equation

HRID 48981 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][N:8]=[C:7]([Cl:10])[C:6]=2[CH:11]=1.CN(C)[C:14]1[O:15][C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[N:19]=1>C(O)(=O)C>[Cl:10][C:7]1[C:6]2[CH:11]=[C:2]([N:1]3[C:16](=[O:24])[CH:17]=[C:18]([C:20]([F:23])([F:22])[F:21])[NH:19][C:14]3=[O:15])[CH:3]=[CH:4][C:5]=2[S:9][N:8]=1

Participants

4

Reactant 2

HCID 1987661,2-Benzisothiazol-5-amine, 3-chloro-HCID 37238622-(dimethylamino)-4-(trifluoromethyl)-6H-1,3-oxazin-6-one

Product 1

HCID 159065603-(3-chloro-1,2-benzisothiazol-5-yl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedioneYield 24.1%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
97.5 °C

Procedure

A mixture of 5-amino-3-chloro-1,2-benzisothiazole (1.10 g) and 2-dimethylamino-4-(trifluoromethyl)-6H-1,3-oxazin-6-one (1.38 g) in acetic acid (15.1 mL) is stirred at 90-105° C. for two hours, cooled to room temperature, and filtered to obtain 0.500 g of the title product as a solid. The resultant filtrate is diluted with water and filtered to obtain an additional 1.11 g of the title product.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered

Sources & evidence

ORD record
ord-abb4745993eb44c580b2e09ff5b169e4
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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