Water → HCID 23144768, compound

HRID 2238824Notes

Reaction equation

HRID 2238824 reaction equation
[NH2:1][C:2]1[S:3][C:4]([Br:12])=[C:5]([C:7]2[O:8][CH:9]=[CH:10][CH:11]=2)[N:6]=1.[C:13](Cl)(=[O:20])[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O>N1C=CC=CC=1.CN(C)C1C=CN=CC=1>[Br:12][C:4]1[S:3][C:2]([NH:1][C:13](=[O:20])[C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)=[N:6][C:5]=1[C:7]1[O:8][CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 3

HCID 962WaterHCID 7412Benzoyl chlorideHCID 12007427HCID 12007427, compound

Product 1

HCID 23144768HCID 23144768, compoundYield 84.2%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolvent

Procedure

Compound g (10.0 g, 40.8 mmol) obtained in Reference Example 7 was dissolved in pyridine (136 mL), and under ice-cooling, 4-dimethylaminopyridine (250 mg, 2.04 mmol) and benzoyl chloride (8.05 mL, 69.4 mmol) were added thereto, followed by stirring at room temperature for 30 minutes. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The organic layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=10:1) to afford N-[5-bromo-4-(2-furyl)thiazol-2-yl]benzamide (12.0 g, 84%) as a white solid.

Workup

  1. temperatureunder ice-cooling
  2. extractionfollowed by extraction with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  4. distillationthe solvent was distilled away under reduced pressure
  5. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-d4f17af94cd44726bf011af8a7e2c9c7
Source dataset
uspto-grants-2010_05
Patent number
US07718808B2

Reaction notes

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