4-Methylmorpholine → HCID 977000, compound

HRID 873592Notes

Reaction equation

HRID 873592 reaction equation
[OH:1]/[N:2]=[C:3](\[NH2:13])/[C:4]1[CH:9]=[CH:8][C:7]([N+:10]([O-:12])=[O:11])=[CH:6][CH:5]=1.CN1CCOCC1.[CH3:21][C:22]([CH3:28])([CH3:27])[CH2:23][C:24](Cl)=O.[F-].C([N+](CCCC)(CCCC)CCCC)CCC>ClCCl.C(OCC)(=O)C>[CH2:23]([C:24]1[O:1][N:2]=[C:3]([C:4]2[CH:5]=[CH:6][C:7]([N+:10]([O-:12])=[O:11])=[CH:8][CH:9]=2)[N:13]=1)[C:22]([CH3:28])([CH3:27])[CH3:21]

Participants

7

Reactant 4

HCID 79724-MethylmorpholineHCID 815143,3-Dimethylbutanoyl chlorideHCID 2724141Tetrabutylammonium FluorideHCID 95829531613-86-1

Product 1

HCID 977000HCID 977000, compound

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (Z)—N′-hydroxy-4-nitrobenzimidamide (0.500 g, 2.76 mmol) in dichloromethane (6 ml) was added 4-methylmorpholine (0.455 ml, 4.14 mmol) followed by 3,3-dimethylbutanoyl chloride (0.422 ml, 3.04 mmol). After 1 hour, the crude reaction mixture was purified by normal phase chromatography and the collected intermediate was dissolved in dichloromethane (8 ml) and treated with tetrabutylammonium fluoride (1.0M in THF) (8.28 ml, 8.28 mmol). After 3 hours at room temperature, the mixture was diluted with ethyl acetate, washed with water, dried over magnesium sulfate, filtered, and concentrated. Normal phase chromatography provided the title compound.

Workup

  1. customthe crude reaction mixture
  2. customwas purified by normal phase chromatography
  3. dissolutionthe collected intermediate was dissolved in dichloromethane (8 ml)
  4. waitAfter 3 hours at room temperature
  5. washwashed with water
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-badd100d10184e1c90799db9cf6065e1
Source dataset
uspto-grants-2015_03
Patent number
US08975398B2

Reaction notes

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