Hydrochloric Acid → 5-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-alpha-ethyl-1,2-benzisothiazole-3-acetonitrile

HRID 1274639Notes

Reaction equation

HRID 1274639 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]([CH2:21][C:22]#[N:23])[C:17]=3[CH:24]=2)[C:3]1=[O:25].I[CH2:27][CH3:28].C(=O)([O-])[O-].[K+].[K+].Cl>CS(C)=O>[CH3:1][N:2]1[C:7]([C:8]([F:10])([F:11])[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]([CH2:27][CH3:28])[C:22]#[N:23])[C:17]=3[CH:24]=2)[C:3]1=[O:25]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 221199235-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetonitrile

Product 1

HCID 221198675-[3,6-Dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-alpha-ethyl-1,2-benzisothiazole-3-acetonitrileYield 28%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of 5-[3,6-dihydro-3-methyl-2,6-dioxo-4-(trifluoromethyl)-1(2H)-pyrimidinyl]-1,2-benzisothiazole-3-acetonitrile (0.730 g, 0.00199 mol) in dimethyl sulfoxide is added iodoethane (0.170 ml, 0.00210 mol) followed by potassium carbonate (0.750 g, 0.00543 mol). The resultant mixture is stirred overnight at room temperature and poured onto a mixture of ice and 5% aqueous hydrochloric acid. The resultant solid is filtered, dried and taken up in a minimal amount of methylene chloride. Flash column chromatography using silica gel and 100% to 99:1 methylene chloride/diethyl ether gives the title compound as a white solid (0.220 g, 28.0%, mp 107-109° C.) which is identified by NMR spectral analysis.

Workup

  1. filtrationThe resultant solid is filtered
  2. customdried

Sources & evidence

ORD record
ord-6d34e56c77e54e74a7fb09ad4e31e9f9
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

Loading…