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Acetonitrile → 1-Methyl-3-[3-(1,3-oxathian-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil

HRID 49014
Notes
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Reaction equation

HRID 49014 reaction equation
[CH3:1][N:2]1[C:7]([C:8]([F:11])([F:10])[F:9])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]=[O:22])[C:17]=3[CH:23]=2)[C:3]1=[O:24].[SH:25][CH2:26][CH2:27][CH2:28]O.[Bi](Cl)(Cl)Cl.C(#N)C>C(OCC)C>[CH3:1][N:2]1[C:7]([C:8]([F:9])([F:10])[F:11])=[CH:6][C:5](=[O:12])[N:4]([C:13]2[CH:14]=[CH:15][C:16]3[S:20][N:19]=[C:18]([CH:21]4[S:25][CH2:26][CH2:27][CH2:28][O:22]4)[C:17]=3[CH:23]=2)[C:3]1=[O:24]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24591Bismuth trichloride2×HCID 882113-Mercaptopropanol2×HCID 178523685-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1, 2-benzisothiazole-3-carboxaldehyde

Product 1

HCID 206341641-Methyl-3-[3-(1,3-oxathian-2-yl)-1,2-benzisothiazol-5-yl]-6-(trifluoromethyl)uracil
Yield 39.2%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-carboxaldehyde (2.86 g, 8.05 mmol), 3-mercapto-1-propanol (0.600 ml, 6.84 mmol), bismuth (III) chloride (0.090 g, 0.285 mol) and acetonitrile is stirred overnight at room temperature. Additional 3-mercapto-1-propanol (0.200 ml, 2.31 mmol) and bismuth (III) chloride are added and the resultant mixture is concentrated in vacuo. The residue is chromatographed with ethyl acetate-hexanes to afford a solid, which is taken up in diethyl ether, washed with water, once with brine and dried over anhydrous magnesium sulfate. Concentration in vacuo affords the title compound as a white solid (1.15 g, 33.2%, mp 125-130° C.) which is identified by NMR spectral analysis.

Workup

  1. concentrationthe resultant mixture is concentrated in vacuo
  2. customThe residue is chromatographed with ethyl acetate-hexanes
  3. customto afford a solid, which
  4. washwashed with water, once with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. concentrationConcentration in vacuo

Sources & evidence

ORD record
ord-eac1b6e5edea4614bc5fba3233bd5158
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