Chlorosuccinimide → HCID 11666112, compound

HRID 2067092Notes

Reaction equation

HRID 2067092 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[CH:23]=[CH:22][C:13]2[N:14]([CH2:18][C:19]([NH2:21])=[O:20])[C:15](=[O:17])[O:16][C:12]=2[C:11]=1[F:24]>S(=O)(=O)(O)O>[Cl:1][C:22]1[C:13]2[N:14]([CH2:18][C:19]([NH2:21])=[O:20])[C:15](=[O:17])[O:16][C:12]=2[C:11]([F:24])=[C:10]([F:9])[CH:23]=1

Participants

4

Reactant 2

HCID 31398Chlorosuccinimide2×HCID 11528709HCID 11528709, compound

Product 1

HCID 11666112HCID 11666112, compoundYield 73%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, N-chlorosuccinimide (0.29 g; 2.19 mmol) is added to a suspension of 2-(6,7-difluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide 18 (0.5 g, 2.19 mmol) and sulfuric acid (90% w/w, 20 ml) at 0° C. The reaction mixture is stirred at room temperature for two days and another portion of N-chlorosuccinimide (0.29 g, 2.19 mmol) is added. After 14 days at room temperature, the reaction mixture is poured carefully into ice. The precipitate is collected by filtration, washed with water and recrystallized EtOH/water (20/80 (v/v)) to afford 0.42 g of a powder which is further purified by column chromatography on reverse phase to give 2-(4-chloro-6,7-difluoro-2-oxo-benzooxazol-3-yl)-acetamide 24 after recrystallization in ethanol.

Workup

  1. waitAfter 14 days at room temperature
  2. additionthe reaction mixture is poured carefully into ice
  3. filtrationThe precipitate is collected by filtration
  4. washwashed with water
  5. customrecrystallized EtOH/water (20/80 (v/v))

Sources & evidence

ORD record
ord-ad0856e2248b443f91b942239e105e6a
Source dataset
uspto-grants-2012_10
Patent number
US08293775B2

Reaction notes

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