N-Iodosuccinimide → 5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamide

HRID 646474Notes

Reaction equation

HRID 646474 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[CH:10]=[C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:12]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:8][N:7]=1)=[O:5])[CH3:2].[I:34]N1C(=O)CCC1=O.[N+]([O-])([O-])=O.[Ce+4].[NH4+].[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O.[N+]([O-])([O-])=O>C(#N)C>[CH2:1]([NH:3][C:4]([C:6]1[C:10]([I:34])=[C:9]([C:11]2[CH:16]=[C:15]([Cl:17])[C:14]([O:18][CH2:19][C:20]3[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=3)=[CH:13][C:12]=2[O:26][CH2:27][C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[O:8][N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 120273N-IodosuccinimideHCID 9869224Ammonium cerium (IV) nitrateHCID 247740415-(2,4-Bis(benzyloxy)-5-chlorophenyl)-N-ethylisoxazole-3-carboxamide

Product 1

HCID 592647675-(2,4-Bis-benzyloxy-5-chloro-phenyl)-4-iodo-isoxazole-3-carboxylic acid ethylamideYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
100 °C

Procedure

5-(2,4-Bis-benzyloxy-5-chloro-phenyl)-isoxazole-3-carboxylic acid ethylamide (0.90 g, 1.94 mmol), N-Iodosuccinimide (0.44 g, 1 equiv.) and Ammonium cerium (IV) nitrate (0.53 g, 0.5 equiv) were suspended in Acetonitrile (55 ml) before heating to reflux (oil bath 100° C.) where upon the mixture became homogeneous. After 18 hrs the solution was cooled and the solvent removed in vaccuo to give a thick orange oil. This was partitioned between DCM (25 ml) and water (10 ml), the organic layer was kept and washed with brine (2×25 ml) before drying over Na2SO4. The DCM was removed in vaccuo to provide 0.88 g (77% yield) of the product as a orange/tan coloured powder.

Workup

  1. temperaturebefore heating
  2. temperatureAfter 18 hrs the solution was cooled
  3. customthe solvent removed in vaccuo
  4. customto give a thick orange oil
  5. customThis was partitioned between DCM (25 ml) and water (10 ml)
  6. washwashed with brine (2×25 ml)
  7. dry with materialbefore drying over Na2SO4
  8. customThe DCM was removed in vaccuo

Sources & evidence

ORD record
ord-ee30a8c086144905a7ef3b0fc9ca5e0d
Source dataset
uspto-grants-2010_04
Patent number
US07705027B2

Reaction notes

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