Dimethylformamide → HCID 66680448, compound

HRID 1626739Notes

Reaction equation

HRID 1626739 reaction equation
C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.[Cl:12][C:13]1[CH:14]=[CH:15][C:16]([NH:23][C:24](=[O:27])[CH2:25]Cl)=[C:17]([CH:22]=1)[C:18]([O:20][CH3:21])=[O:19].[C:28]([C:32]1[CH:33]=[C:34]([OH:38])[CH:35]=[CH:36][CH:37]=1)([CH3:31])([CH3:30])[CH3:29]>C(OCC)(=O)C.O>[C:28]([C:32]1[CH:33]=[C:34]([CH:35]=[CH:36][CH:37]=1)[O:38][CH2:25][C:24]([NH:23][C:16]1[CH:15]=[CH:14][C:13]([Cl:12])=[CH:22][C:17]=1[C:18]([O:20][CH3:21])=[O:19])=[O:27])([CH3:31])([CH3:29])[CH3:30]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 11450Phenol, 3-(1,1-dimethylethyl)-HCID 17550143HCID 17550143, compound

Product 1

HCID 66680448HCID 66680448, compoundYield 30%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

1.59 g (11.5 mmol) of potassium carbonate was added to a DMF (20 mL) solution comprising 1.00 g (3.82 mmol) of methyl 5-chloro-2-[(chloroacetyl)amino]benzoate and 574 mg (3.82 mmol) of 3-tert-butylphenol. The mixture was stirred at 80° C. for 7 hours, and then cooled to room temperature. Water and ethyl acetate were added thereto, and extraction was performed. Thereafter, the organic layer was separated, washed with saturated saline, dried over sodium sulfate, and filtered. After the filtrate was condensed, the obtained crude product was separated and purified by silica gel column chromatography, thereby giving 429 mg of methyl 2-{[(3-tert-butylphenoxy)acetyl]amino}-5-chlorobenzoate (yield: 30%).

Workup

  1. temperaturecooled to room temperature
  2. extractionextraction
  3. customThereafter, the organic layer was separated
  4. washwashed with saturated saline
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. customcondensed
  8. customthe obtained crude product
  9. customwas separated
  10. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-66850aa5aba74fdca5c5381f3d1f2dc2
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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