Potassium Carbonate → HCID 87233628, compound

HRID 564294Notes

Reaction equation

HRID 564294 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:26])[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:13]=1.[CH3:28][C:29]1[CH:34]=[CH:33][C:32]([S:35](OC(C(F)(F)F)C(F)(F)F)(=[O:37])=[O:36])=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C1OCCOCCOCCOCCOCCOC1>C(OCC)(=O)C.CN(C)C=O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][S:35]([C:32]2[CH:33]=[CH:34][C:29]([CH3:28])=[CH:30][CH:31]=2)(=[O:37])=[O:36])[CH:5]=[C:4]([CH3:9])[C:3]=1[NH:10][C:11](=[O:27])[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([NH:18][C:19](=[O:26])[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)[CH:13]=1

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 989162-Propanol, 1,1,1,3,3,3-hexafluoro-, 2-(4-methylbenzenesulfonate)HCID 670053633-Benzamido-N-(2-bromo-4-hydroxy-6-methylphenyl)benzamide

Product 1

HCID 87233628HCID 87233628, compoundYield 13%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
70 °C

Procedure

0.30 g of N-(2-bromo-6-methyl-4-hydroxyphenyl) 3-(benzoylamino)benzamide, 0.23 g of 1,1,1,3,3,3-hexafluoroisopropyl p-toluenesulfonate, 0.19 g of potassium carbonate and 0.03 g of 18-crown-6 ether were added to 5 ml of N,N-dimethylformamide, and the resulting mixture was stirred at 70° C. for 6 hours. 100 ml of ethyl acetate was added thereto and washed with water (50 ml×2). The organic phase was dried over anhydrous magnesium sulfate and the solvent was removed under a reduced pressure to obtain a residue. The resulting residue was purified by silica gel column chromatography (n-hexane EtOAc=3:1) to obtain 0.05 g of the desired product (Yield: 13%).

Workup

  1. washwashed with water (50 ml×2)
  2. dry with materialThe organic phase was dried over anhydrous magnesium sulfate
  3. customthe solvent was removed under a reduced pressure
  4. customto obtain a residue
  5. customThe resulting residue was purified by silica gel column chromatography (n-hexane EtOAc=3:1)

Sources & evidence

ORD record
ord-4225bdb7aa724cfb9a94fdcc0e578ebf
Source dataset
uspto-grants-2011_11
Patent number
US08067638B2

Reaction notes

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