Chlorosuccinimide → HCID 67121071, compound

HRID 1510419Notes

Reaction equation

HRID 1510419 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][N:11]=[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:9]=2)=[CH:4][CH:3]=1.[Cl:18]N1C(=O)CCC1=O>C(O)(=O)C>[Cl:18][C:9]1[C:10]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[N:11][O:12][C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 13035537Ethyl 5-(4-chlorophenyl)-1,2-oxazole-3-carboxylate

Product 1

HCID 67121071HCID 67121071, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of ethyl 5-(4-chlorophenyl)isoxazole-3-carboxylate (250 mg, 1.0 mmol) and N-chlorosuccinimide (267 mg, 2.0 mmol) in acetic acid (5 mL) was heated to reflux for 3 days. The reaction mixture was then allowed to cool to room temperature, poured over ice and the resulting pale yellow solid was collected, washed with portions of water, and dried to obtain ethyl 4-chloro-5-(4-chlorophenyl)isoxazole-3-carboxylate (234 mg, 0.82 mmol).

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 3 days
  3. additionpoured over ice
  4. customthe resulting pale yellow solid was collected
  5. washwashed with portions of water
  6. customdried

Sources & evidence

ORD record
ord-881bf45dafd84fbbae18c9d16488a489
Source dataset
uspto-grants-2012_07
Patent number
US08211927B2

Reaction notes

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