Triethylamine → HCID 22448996, compound

HRID 2186731Notes

Reaction equation

HRID 2186731 reaction equation
O[CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:9]=2[O:8][CH2:7][C:6]1=[O:22].C(N(CC)CC)C.CS(Cl)(=O)=O.[N-:35]=[N+:36]=[N-:37].[Na+]>ClCCl.C(Cl)(Cl)Cl.CN(C=O)C.C(OCC)(=O)C>[N:35]([CH2:2][CH2:3][CH2:4][N:5]1[C:10]2[CH:11]=[CH:12][CH:13]=[C:14]([O:15][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][O:17]3)[C:9]=2[O:8][CH2:7][C:6]1=[O:22])=[N+:36]=[N-:37]

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 33557Sodium AzideHCID 22448928HCID 22448928, compound

Product 1

HCID 22448996HCID 22448996, compoundYield 96%

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

4-(3-hydroxypropyl)-3-oxo-8-(tetrahydropyran-2-yloxy)-3,4-dihydro-2H-1,4-benzoxazine (2.0 g) was dissolved in dichloromethane (20 ml), and triethylamine (1.27 ml) and a methanesulfonyl chloride (0.6 ml) were added to the resultant solution at 0° C., followed by stirring for 2 hours. The reaction solution was diluted with chloroform, washed with saturated brine, and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off under reduced pressure to obtain a crude mesyl compound. The crude mesyl compound was dissolved in DMF (20 ml), and sodium azide (510 mg) was added to the resultant solution, and the mixture was stirred at room temperature for 15 hours. The reaction solution was diluted with ethyl acetate, washed with saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure, and the resultant residue was purified by column chromatography (silica gel: ethyl acetate/n-hexane=1:9) to obtain the object compound (2.07 g, yield 96%).

Workup

  1. washwashed with saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. distillationThen, the solvent was distilled off under reduced pressure
  4. customto obtain a crude mesyl compound
  5. stirringthe mixture was stirred at room temperature for 15 hours
  6. washwashed with saturated brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off under reduced pressure
  9. customthe resultant residue was purified by column chromatography (silica gel: ethyl acetate/n-hexane=1:9)

Sources & evidence

ORD record
ord-f695e9e1e60f4592bbb0bdc940db246b
Source dataset
uspto-grants-2002_06
Patent number
US06407096B1

Reaction notes

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