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Dichloromethane → 3-[3-(1,3-Dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 49005
Notes
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Reaction equation

HRID 49005 reaction equation
BrC(Br)[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:22])([F:21])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1.ClCCl.[CH3:29][O:30][CH2:31][O:32][CH3:33]>FC(F)(F)S([O-])(=O)=O.[Ag+].C(O)CO>[O:30]1[CH2:29][CH2:33][O:32][CH:31]1[C:3]1[C:7]2[CH:8]=[C:9]([N:12]3[C:17](=[O:18])[CH:16]=[C:15]([C:19]([F:21])([F:22])[F:20])[N:14]([CH3:23])[C:13]3=[O:24])[CH:10]=[CH:11][C:6]=2[S:5][N:4]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 8020DimethoxymethaneHCID 221198393-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 206342023-[3-(1,3-Dioxolan-2-yl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracilYield 17.5%

Reagents, catalysts & solvents 2

HCID 76223
Silver(I) trifluoromethanesulfonate
Catalyst
4×
HCID 174Ethylene GlycolSolvent3×

Procedure

A mixture of 3-[3-(dibromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (0.500 g, 10.0 mmol), silver trifluoromethanesulfonate (0.500 g, 19.5 mmol), ethylene glycol (5.00 ml), dichloromethane and dimethoxymethane is stirred three days at room temperature and treated with additional silver trifluoromethanesulfonate (0.300 g, 11.7 mmol). The resultant mixture is stirred one day at room temperature and treated with additional silver trifluoromethanesulfonate (0.400 g, 15.6 mmol) and ethylene glycol (1.00 ml), stirred another day at room temperature and treated again with silver trifluoromethanesulfonate (0.300 g, 11.7 mmol) and ethylene glycol (1.0 ml). After stirring an additional day the mixture is filtered. The filtrate is diluted with dichloromethane, washed with water, dried over anhydrous magnesium sulfate and concentrated in vacuo. The residue is triturated with hexanes-ethyl acetate to afford the title compound as a white solid (0.070 g, 17.5%, mp 213-216° C.) which is identified by NMR spectral analysis.

Workup

  1. stirringstirred another day at room temperature
  2. stirringAfter stirring an additional day the mixture
  3. filtrationis filtered
  4. additionThe filtrate is diluted with dichloromethane
  5. washwashed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. concentrationconcentrated in vacuo
  8. customThe residue is triturated with hexanes-ethyl acetate

Sources & evidence

ORD record
ord-16b4da2259f54c529f075d0511a069de
Source dataset
uspto-grants-2004_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06706663B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes