Sodium Iodide → HCID 22010587, compound

HRID 323154Notes

Reaction equation

HRID 323154 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:33]=[CH:32][CH:31]=[CH:30][C:18]=3C(N(C)C3C=CC=CC=3O)=O)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1.[C:34](=[O:37])([O-])[O-].[K+].[K+].Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47].[I-].[Na+].[CH3:53][N:54]([CH3:57])[CH:55]=[O:56]>>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]([C:14]([NH:16][C:17]3[CH:33]=[CH:32][C:31]([C:55]([N:54]([CH3:57])[C:53]4[CH:4]=[CH:3][CH:2]=[CH:1][C:34]=4[O:37][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][C:46]([O:48][CH2:49][CH3:50])=[O:47])=[O:56])=[CH:30][CH:18]=3)=[O:15])=[CH:10][CH:11]=[CH:12][CH:13]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 5238Sodium IodideHCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 117544Ethyl 6-bromohexanoateHCID 22010724HCID 22010724, compound

Product 1

HCID 22010587HCID 22010587, compound

Procedure

To a solution of 4′-methylbiphenyl-2-carboxamido-N-methyl-N-(2-hydroxyphenyl)benzamide (263 mg) in N,N-dimethylformamide (15 ml) was added potassium carbonate (250 mg), ethyl 6-bromohexanoate (161 mg) and sodium iodide (cat.) at 60° C. The reaction mixture was stirred at same temperature for 13 hours. The reaction mixture was cooled in an ice bath and quenched with 1N hydrochloric acid (4 ml) and water (20 ml). The mixture was extracted with ethyl acetate. The organic phase was washed with water and brine. The organic solution was dried over magnesium sulfate. The solvent was removed by evaporation to give 4-(4′-methylbiphenyl-2-carboxamido)-N-methyl-N-[2-(5-ethoxycarbonylpentyloxy)phenyl]benzamide (380 mg).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath
  2. customquenched with 1N hydrochloric acid (4 ml) and water (20 ml)
  3. extractionThe mixture was extracted with ethyl acetate
  4. washThe organic phase was washed with water and brine
  5. dry with materialThe organic solution was dried over magnesium sulfate
  6. customThe solvent was removed by evaporation

Sources & evidence

ORD record
ord-04e23e8bc62845f0b32a0707b16d939b
Source dataset
uspto-grants-2001_04
Patent number
US06211242B1

Reaction notes

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