Benzene → HCID 21535145, compound

HRID 1076930Notes

Reaction equation

HRID 1076930 reaction equation
[H-].[Na+].[CH3:3][S:4][C:5]1[CH:6]=[C:7]([NH:11][C:12](=[O:16])[CH2:13][CH2:14]Cl)[CH:8]=[CH:9][CH:10]=1.C1C=CC=CC=1>C(Cl)(Cl)(Cl)Cl>[CH3:3][S:4][C:5]1[CH:6]=[C:7]([N:11]2[CH2:14][CH2:13][C:12]2=[O:16])[CH:8]=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 24758Sodium hydrideHCID 20115730HCID 20115730, compound

Product 1

HCID 21535145HCID 21535145, compound

Reagents, catalysts & solvents 1

HCID 5943Carbon TetrachlorideSolvent

Procedure

Sodium hydride (0.1 mole; 57% dispersion in mineral oil) is charged into a glass reaction flask. The mineral oil is removed by washing the sodium hydride with benzene, and dimethyl sulfoxide (50 ml) is thereafter slowly added with stirring. The mixture is stirred until no more hydrogen gas evolves. A solution of N-(3-methylthiophenyl)-β-chloropropionamide (0.08 mole) in carbon tetrachloride (50 ml) is added dropwise to the reaction flask with stirring while maintaining the temperature of the reaction mixture below about 30°C. After the addition is completed the reaction mixture is allowed to stand at room temperature for a period of about 8 hours. After this time benzene is added and the reaction mixture is washed with water and aqueous sodium bicarbonate. The washed mixture is then dried over anhydrous magnesium sulfate, is filtered, and is stripped of solvents under reduced pressure to yield the desired product N-(3-methylthiophenyl)-2-azetidinone as the residue.

Workup

  1. customThe mineral oil is removed
  2. washby washing the sodium hydride with benzene, and dimethyl sulfoxide (50 ml)
  3. additionis thereafter slowly added
  4. stirringThe mixture is stirred until no more hydrogen gas evolves
  5. stirringwith stirring
  6. temperaturewhile maintaining the temperature of the reaction mixture below about 30°C
  7. additionAfter the addition
  8. washthe reaction mixture is washed with water and aqueous sodium bicarbonate
  9. dry with materialThe washed mixture is then dried over anhydrous magnesium sulfate
  10. filtrationis filtered

Sources & evidence

ORD record
ord-a0eef9dc0fd44c47ab5493df5f3bab15
Source dataset
uspto-grants-1976_05
Patent number
US03958974

Reaction notes

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