Dimethylformamide → HCID 66680314, compound

HRID 1626736Notes

Reaction equation

HRID 1626736 reaction equation
[C:1](=[O:4])([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].[Br:28][C:29]1[CH:34]=C[CH:32]=[CH:31][C:30]=1O>C(OCC)(=O)C.O>[Br:28][C:29]1[CH:34]=[C:1]([CH:32]=[CH:31][CH:30]=1)[O:4][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]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 72442-BromophenolHCID 11430Potassium CarbonateHCID 17550143HCID 17550143, compound

Product 1

HCID 66680314HCID 66680314, compoundYield 73%

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 0.66 g (3.82 mmol) of bromophenol, and the mixture was heated while stirring at 80° C. for 2 hours. The mixture was cooled to room temperature, and water and ethyl acetate were added thereto. After the mixture was extracted, the organic layer was separated, washed with saturated saline, dried over sodium sulfate, filtered, condensed, and dried under reduced pressure. IPE was added to the residue, and powders were collected by filtration, washed with IPE, and dried under reduced pressure at 50° C. for 5 hours, thereby giving 1.11 g of methyl 2-{[(3-bromophenoxy)acetyl]amino-}-5-chlorobenzoate (yield: 73%).

Workup

  1. temperaturethe mixture was heated
  2. temperatureThe mixture was cooled to room temperature
  3. extractionAfter the mixture was extracted
  4. customthe organic layer was separated
  5. washwashed with saturated saline
  6. dry with materialdried over sodium sulfate
  7. filtrationfiltered
  8. customcondensed
  9. customdried under reduced pressure
  10. additionIPE was added to the residue, and powders
  11. filtrationwere collected by filtration
  12. washwashed with IPE
  13. customdried under reduced pressure at 50° C. for 5 hours

Sources & evidence

ORD record
ord-b0465a38b7114337aa2aee3ac0892680
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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