Methyl iodide → 3-[4-Chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

HRID 1419708Notes

Reaction equation

HRID 1419708 reaction equation
CI.[C:3](=[O:6])([O-])[O-].[K+].[K+].[Cl:9][C:10]1[C:15]2[N:16]=[C:17]([O:19][CH2:20][CH2:21][CH3:22])[S:18][C:14]=2[C:13]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[NH:25][C:24]2=O)=[C:12]([F:35])[CH:11]=1>CC(CC)=O>[Cl:9][C:10]1[C:15]2[N:16]=[C:17]([O:19][CH2:20][CH2:21][CH3:22])[S:18][C:14]=2[C:13]([N:23]2[C:28](=[O:29])[CH:27]=[C:26]([C:30]([F:31])([F:33])[F:32])[N:25]([CH3:24])[C:3]2=[O:6])=[C:12]([F:35])[CH:11]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 153461793-[4-Chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 153461803-[4-Chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-1-methyl-6-trifluoromethyl-2,4(1H, 3H)-pyrimidinedione

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

1.7 g of methyl iodide were added dropwise at about 20° C. to a mixture of 200 ml of absolute ethyl methyl ketone, 1.7 g of potassium carbonate and 5.0 g of 3-[4-chloro-6-fluoro-2-propoxybenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione (compound I.8). Stirring was carried out for 12 hours at room temperature, after which the insoluble components were filtered off. The clear solution obtained was evaporated down. The residue was then taken up in water, after which the solution was neutralized with dilute hydrochloric acid. The product was then extracted with ethyl acetate. The ester phase was finally dried over sodium sulfate and then evaporated down. The purification of the crude product thus obtained was carried out by chromatography over silica gel (eluent: 9:1 cyclohexane/methyl tert-butyl ether). Yield: 1.0 g.

Workup

  1. filtrationafter which the insoluble components were filtered off
  2. customThe clear solution obtained
  3. customwas evaporated down
  4. extractionThe product was then extracted with ethyl acetate
  5. dry with materialThe ester phase was finally dried over sodium sulfate
  6. customevaporated down
  7. customThe purification of the crude product
  8. customthus obtained

Sources & evidence

ORD record
ord-db5739705e2c47a3904a1970c874879d
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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