Oxalyl chloride → HCID 86690015, compound

HRID 1186743Notes

Reaction equation

HRID 1186743 reaction equation
[C:1](Cl)(=[O:5])[C:2](Cl)=[O:3].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([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:11][CH:10]=1.C(=O)([O-])O.[Na+]>O1CCCC1>[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([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:11][CH:10]=1

Participants

5

Reactant 3

HCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 86690016HCID 86690016, compound

Product 1

HCID 86690015HCID 86690015, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To an anhydrous tetrahydrofuran (5 mL) solution of oxalyl chloride (0.12 mL) was added dropwise an anhydrous tetrahydrofuran (10 mL) solution of N2-(4-methoxyphenyl)naphthalene-1,2-diamine (322 mg, 1.22 mmol) under cooling in an ice-bat. The mixture was stirred under cooling in 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. The solvent was removed by evaporation under reduced pressure. The obtained solid was filtered. The crude crystal was washed with ethyl acetate and hexane to obtain the titled compound as a slightly off-white crystal (220 mg, yield 56%).

Workup

  1. temperatureunder cooling in ice-bath for 30 minutes
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  4. customThe solvent was removed by evaporation under reduced pressure
  5. filtrationThe obtained solid was filtered
  6. washThe crude crystal was washed with ethyl acetate and hexane

Sources & evidence

ORD record
ord-d7c502255c6849c9a09d8e4c3f74ae3f
Source dataset
uspto-grants-2014_03
Patent number
US08673915B2

Reaction notes

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