Dimethylformamide → HCID 66680269, compound

HRID 1626726Notes

Reaction equation

HRID 1626726 reaction equation
[O:1]1[CH:5]=[CH:4][C:3]([C:6]2[CH:7]=[C:8]([CH2:12][C:13]([OH:15])=O)[CH:9]=[CH:10][CH:11]=2)=[CH:2]1.CN(C=O)C.C(Cl)(=O)C(Cl)=O.[NH2:27][C:28]1[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][C:29]=1[C:30]([O:32][CH3:33])=[O:31]>C1COCC1.C(OCC)(=O)C.CC(N(C)C)=O>[Cl:38][C:35]1[CH:36]=[CH:37][C:28]([NH:27][C:13](=[O:15])[CH2:12][C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([C:3]3[CH:4]=[CH:5][O:1][CH:2]=3)[CH:7]=2)=[C:29]([CH:34]=1)[C:30]([O:32][CH3:33])=[O:31]

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 78878Methyl 2-amino-5-chlorobenzoateHCID 22326463HCID 22326463, compound

Product 1

HCID 66680269HCID 66680269, compoundYield 89%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolventHCID 31374DimethylacetamideSolvent

Procedure

0.25 g (1.2 mmol) of [3-(furan-3-yl)phenyl]acetic acid, a catalytic amount of DMF, and 0.36 g (1.7 mmol) of oxalyl chloride were stirred in 10 mL of THF at 0° C. for 1.5 hours. Thereafter, the solvent was distilled off under reduced pressure. 0.23 g (1.2 mmol) of methyl 2-amino-5-chlorobenzoate and 5 mL of DMAc were added to the residue at 0° C., and the mixture was stirred at room temperature for 1.5 hours. After the completion of the reaction, the mixture was diluted with ethyl acetate, washed with an aqueous sodium hydrogen carbonate solution and saturated saline, and dried over anhydrous sodium sulfate. The obtained crude product was separated and purified by silica gel column chromatography, thereby giving 0.3 g of methyl 5-chloro-2-({[3-(furan-3-yl)phenyl]acetyl}amino)benzoate (yield: 89%).

Workup

  1. distillationThereafter, the solvent was distilled off under reduced pressure
  2. customAfter the completion of the reaction
  3. washwashed with an aqueous sodium hydrogen carbonate solution and saturated saline
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe obtained crude product
  6. customwas separated
  7. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-758276898cca4f80b1691bba0d866349
Source dataset
uspto-grants-2014_07
Patent number
US08785473B2

Reaction notes

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