Hydrochloric Acid → HCID 22119859, compound

HRID 1274611Notes

Reaction equation

HRID 1274611 reaction equation
[H-].[Na+].[C:3]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])(=[O:8])[CH2:4][C:5]([CH3:7])=[O:6].Br[CH2:15][C:16]1[C:20]2[CH:21]=[C:22]([N:25]3[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]3=[O:37])[CH:23]=[CH:24][C:19]=2[S:18][N:17]=1.Cl>O1CCCC1.CS(C)=O.C(Cl)Cl.C(OCC)C>[C:5]([CH:4]([CH2:15][C:16]1[C:20]2[CH:21]=[C:22]([N:25]3[C:30](=[O:31])[CH:29]=[C:28]([C:32]([F:35])([F:34])[F:33])[N:27]([CH3:36])[C:26]3=[O:37])[CH:23]=[CH:24][C:19]=2[S:18][N:17]=1)[C:3]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])(=[O:6])[CH3:7]

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 15538Tert-butyl acetoacetateHCID 24758Sodium hydrideHCID 22119928HCID 22119928, compound

Product 1

HCID 22119859HCID 22119859, compound

Reagents, catalysts & solvents 4

HCID 679Dimethyl SulfoxideSolventHCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A mixture of sodium hydride (60% in oil, 0.293 g, 7.33 mmol) in tetrahydrofuran is cooled to 0° C., treated dropwise with a solution of tert-butyl acetoacetate (1.00 mL, 6.03 mmol) in tetrahydrofuran, and stirred for several minutes. The resultant mixture is added dropwise to a solution of 3-[3-(bromomethyl)-1,2-benzisothiazol-5-yl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione (1.40 g, 3.33 mmol) in methyl sulfoxide. After the addition is complete, the reaction mixture is poured into an ice-water mixture containing a trace of 10% hydrochloric acid. The resultant aqueous mixture is extracted with methylene chloride. the organic extracts are combined, dried over anhydrous magnesium sulfate, and concentrated in vacuo to obtain an oil. Column chromatography of the oil using silica gel and 0%, 2%, 3%, and 15% diethyl ether in methylene chloride solutions gives the title product as a solid, mp 76-78° C.

Workup

  1. additionAfter the addition
  2. extractionThe resultant aqueous mixture is extracted with methylene chloride
  3. dry with materialdried over anhydrous magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customto obtain an oil

Sources & evidence

ORD record
ord-4509ce740cbb4f1e803b4b59b4a1375c
Source dataset
uspto-grants-2000_12
Patent number
US06156700

Reaction notes

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