Acetyl chloride → HCID 14099493, compound

HRID 1904166Notes

Reaction equation

HRID 1904166 reaction equation
[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:9]3[C:13](=[O:14])[C:12]([CH3:15])=[C:11]([CH3:16])[CH:10]3[OH:17])[S:8][C:4]=2[CH:3]=1.[H-].[Na+].[C:22](Cl)(=[O:24])[CH3:23]>O1CCCC1>[F:1][C:2]1[CH:19]=[CH:18][C:5]2[N:6]=[C:7]([N:9]3[CH:10]([O:17][C:22](=[O:24])[CH3:23])[C:11]([CH3:16])=[C:12]([CH3:15])[C:13]3=[O:14])[S:8][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 24758Sodium hydrideHCID 14099492HCID 14099492, compound

Product 1

HCID 14099493HCID 14099493, compoundYield 88.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

N-(6-fluoro-2-benzothiazolyl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (1.39 g) was added to tetrahydrofuran (30 ml) and sodium hydride (0.18 g) at room temperature. The mixture was refluxed for 15 minutes, and then cooled to room temperature. A solution of acetyl chloride (0.79 g) in tetrahydrofuran (10 ml) was added dropwise. After the mixture was refluxed for 3 hours, the solvent was evaporated. The residue was mixed with water, and extracted with chloroform. The chloroform extract was dried over anhydrous magnesium sulfate, and evaporated to dryness under reduced pressure. The solid residue was washed with a small amount of diethyl ether to give the desired N-(6-fluoro-2-benzothiazolyl)-2-oxo-3,4-dimethyl-5-acetyloxy-2,5-dihydropyrrole (1.42 g). m.p. 180°-183° C.

Workup

  1. temperatureThe mixture was refluxed for 15 minutes
  2. temperatureAfter the mixture was refluxed for 3 hours
  3. customthe solvent was evaporated
  4. additionThe residue was mixed with water
  5. extractionextracted with chloroform
  6. extractionThe chloroform extract
  7. dry with materialwas dried over anhydrous magnesium sulfate
  8. customevaporated to dryness under reduced pressure
  9. washThe solid residue was washed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-652210b8416b40a685809a9f9152cbaa
Source dataset
uspto-grants-1989_06
Patent number
US04836844

Reaction notes

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