Dichloromethane → HCID 60924826, compound

HRID 627509Notes

Reaction equation

HRID 627509 reaction equation
[CH3:1][C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[CH:7][C:3]=1[C:4](O)=[O:5].C(Cl)Cl.C(C1NC=CN=1)(C1NC=CN=1)=O.Cl.[CH3:28][NH:29][O:30][CH3:31]>CN(C=O)C>[CH3:31][O:30][N:29]([CH3:28])[C:4](=[O:5])[C:3]1[CH:7]=[CH:8][C:9]([CH3:11])=[N:10][C:2]=1[CH3:1]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 117152032,6-Dimethylnicotinic acid

Product 1

HCID 60924826HCID 60924826, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a flask containing 2,6-dimethylnicotinic acid (2.80 g, 18.5 mmol) was added CH2Cl2 and DMF (6 mL). The suspension was stirred at room temperature as carbonyl diimidazole (3.50 g, 21.6 mmol) was added. The suspension remained throughout the day and was allowed to stir overnight at room temperature. After 18 hours, N,O-dimethylhydroxylamine hydrochloride (3.00 g, 30.8 mmol) was introduced and the mixture was stirred at room temperature again for 24 hours. The reaction mixture was quenched with water and 1 N NaOH, and extracted with CH2Cl2 (4×50 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated to give a colorless oil. Flash chromatography on silica gel (50% EtOAc-hexane) afforded the title compound as a colorless oil.

Workup

  1. additionwas added
  2. waitAfter 18 hours
  3. stirringthe mixture was stirred at room temperature again for 24 hours
  4. customThe reaction mixture was quenched with water and 1 N NaOH
  5. extractionextracted with CH2Cl2 (4×50 mL)
  6. washThe combined organics were washed with brine
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto give a colorless oil

Sources & evidence

ORD record
ord-78fa375628204ccbbb0ccc353510142f
Source dataset
uspto-grants-2016_04
Patent number
US09309222B2

Reaction notes

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