Oxalyl chloride → HCID 56640372, compound

HRID 1186723Notes

Reaction equation

HRID 1186723 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[CH:10]=[C:11]([NH:15][C:16]2[C:17]([NH2:26])=[C:18]3[C:23](=[CH:24][CH:25]=2)[CH:22]=[CH:21][CH:20]=[CH:19]3)[CH:12]=[CH:13][CH:14]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:10]=[C:11]([N:15]2[C:16]3[CH:25]=[CH:24][C:23]4[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=4[C:17]=3[NH:26][C:2](=[O:3])[C:1]2=[O:5])[CH:12]=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 86689993HCID 86689993, compound

Product 1

HCID 56640372HCID 56640372, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an anhydrous tetrahydrofuran (10 mL) solution of oxalyl chloride (162 μL, 1.89 mmol) was dropwise added an anhydrous tetrahydrofuran (10 mL) solution of N2-(3-methoxyphenyl)naphthalene-1,2-diamine (500 mg, 1.89 mmol) under cooling in an ice-bath. The mixture was stirred under cooling in an ice-bath for 30 minutes and at room temperature for one hour. The reaction mixture was poured into a saturated aqueous sodium hydrogen carbonate solution, and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and purified by silica gel chromatography (chloroform/methanol=97/3) after removing the solvent by evaporation under reduced pressure. The obtained solid was washed with ethyl acetate/methanol (=1/1) to obtain the titled compound as a slightly beige crystal (572 mg, yield 95%).

Workup

  1. temperatureunder cooling in an ice-bath
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. custompurified by silica gel chromatography (chloroform/methanol=97/3)
  5. customafter removing the solvent
  6. customby evaporation under reduced pressure
  7. washThe obtained solid was washed with ethyl acetate/methanol (=1/1)

Sources & evidence

ORD record
ord-7e1f177f52ed48458d1cb4de12f55571
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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