Methanol → 3-[3[4-Methoxy-2-(ethylimino)-5-oxo-4-imidazolidinyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracil

HRID 48999Notes

Reaction equation

HRID 48999 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]([C:21](=O)[C:22](OC)=[O:23])[C:17]=3[CH:27]=2)[C:3]1=[O:28].Cl.[CH2:30]([NH:32][C:33]([NH2:35])=[NH:34])[CH3:31].[C:36](=O)(O)[O-:37].[Na+].CO>O>[CH3:36][O:37][C:21]1([C:18]2[C:17]3[CH:27]=[C:13]([N:4]4[C:5](=[O:12])[CH:6]=[C:7]([C:8]([F:10])([F:11])[F:9])[N:2]([CH3:1])[C:3]4=[O:28])[CH:14]=[CH:15][C:16]=3[S:20][N:19]=2)[C:22](=[O:23])[NH:35][C:33](=[N:32][CH2:30][CH3:31])[NH:34]1

Participants

6

Reactant 4

HCID 887MethanolHCID 516892Sodium BicarbonateHCID 20634280Methyl 5-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylateHCID 178464621HCID 178464621, compound

Product 1

HCID 1358436663-[3[4-Methoxy-2-(ethylimino)-5-oxo-4-imidazolidinyl]-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)uracilYield 63.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of methyl 5-[3-,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-glyoxylate (0.0820 g, 1.98 mmol), ethyl guanidine hydrochloride (0.270 g, 2.18 mmol), sodium bicarbonate (0.180 g, 2.14 mmol) and methanol is stirred overnight at reflux, cooled to room temperature and poured into water. The resultant suspension is stirred 20 minutes and filtered with cold water wash to afford the title compound as a white solid (0.610 g, 63.9%, mp 257° C.) which is identified by NMR spectral analysis.

Workup

  1. temperatureat reflux
  2. filtrationfiltered with cold water
  3. washwash

Sources & evidence

ORD record
ord-ee636c16b7f94b38a52661005635854c
Source dataset
uspto-grants-2004_03
Patent number
US06706663B2

Reaction notes

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