Chlorosuccinimide → HCID 11680337, compound

HRID 2067091Notes

Reaction equation

HRID 2067091 reaction equation
[Cl:1]N1C(=O)CCC1=O.[F:9][C:10]1[C:18]2[O:17][C:16](=[O:19])[N:15]([CH2:20][C:21]([NH2:23])=[O:22])[C:14]=2[CH:13]=[CH:12][CH:11]=1>S(=O)(=O)(O)O>[Cl:1][C:11]1[CH:12]=[CH:13][C:14]2[N:15]([CH2:20][C:21]([NH2:23])=[O:22])[C:16](=[O:19])[O:17][C:18]=2[C:10]=1[F:9]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11629847HCID 11629847, compound

Product 1

HCID 11680337HCID 11680337, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

In a three neck flask, fitted with a magnetic stirrer, under inert atmosphere, N-chlorosuccinimide (0.635 g, 4.75 mmol) is added to a suspension of 2-(7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide 12 (1 g, 4.75 mmol) and sulfuric acid (90% w/w; 20 ml) at 0° C. The reaction is stirred 5 days then poured carefully into ice. The precipitate is collected by filtration and washed with water. The residue is recrystallized in EtOH/water (20/80 (v/v)) to afford 0.54 g of 2-(6-chloro-7-fluoro-2-oxo-1,3-benzoxazol-3(2H)-yl)acetamide 19.

Workup

  1. additionthen poured carefully into ice
  2. filtrationThe precipitate is collected by filtration
  3. washwashed with water
  4. customThe residue is recrystallized in EtOH/water (20/80 (v/v))

Sources & evidence

ORD record
ord-ae594588e7b24b5898f0c3ec6aa7cc4c
Source dataset
uspto-grants-2012_10
Patent number
US08293775B2

Reaction notes

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