Dimethylformamide → 6-Acetylbenzoselenazolinone

HRID 5915

Reaction equation

HRID 5915 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].CN(C)C=O.[Se:10]1(=[O:19])[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[N:12]=[CH:11]1.[C:20](Cl)(=[O:22])[CH3:21]>>[C:20]([C:16]1[CH:17]=[CH:18][C:13]2[N:12]=[CH:11][Se:10](=[O:19])[C:14]=2[CH:15]=1)(=[O:22])[CH3:21]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 87879929Benzoselenazolinone

Product 1

HCID 1317181736-Acetylbenzoselenazolinone

Procedure

12 grams (0.09 mol) of aluminum chloride are introduced into a ground-necked flask. 3.1 cm3 (0.04 mol) of dimethylformamide are added dropwise with stirring. After cooling, two grams (0.01 mol) of benzoselenazolinone are added and the mixture is homogenized. It is heated to 70°-80° C. on an oil bath with stirring, and 0.01 to 0.012 mol of acetyl chloride is then added. heating is maintained at a temperature of 80°-90° C. for a time T of approximately 4 h 30 min. The mixture is hydrolyzed on crushed ice. The product is drained, dried, and washed with boiling cyclohexane and recrystallized in toluene.

Workup

  1. temperatureAfter cooling
  2. stirringthe mixture is homogenized
  3. temperatureIt is heated to 70°-80° C. on an oil bath
  4. stirringwith stirring
  5. temperatureheating
  6. temperatureis maintained at a temperature of 80°-90° C. for a time T of approximately 4 h 30 min
  7. customon crushed ice
  8. customdried
  9. washwashed with boiling cyclohexane
  10. customrecrystallized in toluene

Sources & evidence

ORD record
ord-1d3413e2368040c69f7c5420a1d9dcb4
Source dataset
uspto-grants-1993_09
Patent number
US05246951

Linked notes

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