2(3H)-Benzoxazolone → 6-(3-Chloropropanoyl)-1,3-benzoxazol-2(3H)-one

HRID 654433Notes

Reaction equation

HRID 654433 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[CH:5]1[CH:6]=[CH:7][C:8]2[O:14][C:12](=[O:13])[NH:11][C:9]=2[CH:10]=1.[Cl:15][CH2:16][CH2:17][C:18](Cl)=[O:19]>CN(C)C=O>[Cl:15][CH2:16][CH2:17][C:18]([C:6]1[CH:5]=[CH:10][C:9]2[NH:11][C:12](=[O:13])[O:14][C:8]=2[CH:7]=1)=[O:19]

Participants

5

Reactant 3

HCID 60432(3H)-BenzoxazoloneHCID 693643-Chloropropionyl chlorideHCID 6451240Aluminum(III) Chloride

Product 1

HCID 117908766-(3-Chloropropanoyl)-1,3-benzoxazol-2(3H)-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

56.1 g (0.42 mole) of aluminum chloride are weighed into a ground-necked flask, 10 cm3 of dimethylformamide are then added using a dropping funnel and the mixture is left stirring until it becomes homogeneous. 8.1 g (0.06 mole) of benzoxazolinone are then added and the mixture is left stirring for 10 minutes before adding 7 cm3 (0.072 mole) of 3-chloropropionic acid chloride. This mixture is maintained in an oil bath at 80°-85° C. for approximately 2 hours 30 minutes. After cooling, the reaction mixture is poured into ice-cold water. The precipitate is drained and washed with water to neutrality. The product is recrystallized in ethanol.

Workup

  1. waitthe mixture is left
  2. waitthe mixture is left
  3. stirringstirring for 10 minutes
  4. temperatureThis mixture is maintained in an oil bath at 80°-85° C. for approximately 2 hours 30 minutes
  5. temperatureAfter cooling
  6. additionthe reaction mixture is poured into ice-cold water
  7. washwashed with water to neutrality
  8. customThe product is recrystallized in ethanol

Sources & evidence

ORD record
ord-115e79cdb56f45cb9e47650fe4e039df
Source dataset
uspto-grants-1992_07
Patent number
US05132305

Reaction notes

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