Nitrogen → 2-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl azide

HRID 1189363Notes

Reaction equation

HRID 1189363 reaction equation
N#N.[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18](Cl)=[O:19])[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1.[N-:21]=[N+:22]=[N-:23].[Na+]>CC(C)=O.O>[CH3:3][C:4]1([CH2:9][CH2:10][CH2:11][CH2:12][C:13]2[O:14][CH:15]=[C:16]([C:18]([N:21]=[N+:22]=[N-:23])=[O:19])[N:17]=2)[O:8][CH2:7][CH2:6][O:5]1

Participants

6

Reactant 3

HCID 947NitrogenHCID 33557Sodium AzideHCID 866649012-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride

Product 1

HCID 866649022-[4-(2-Methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl azide

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

In a flame dried round-bottomed flask equipped with a magnetic stir bar and under inert atmosphere (N2), this crude 2-[4-(2-methyl-[1,3]dioxolan-2-yl)-butyl]-oxazole-4-carbonyl chloride was dissolved in acetone (18.0 mL). The solution was cooled to 0° C. and a solution of sodium azide (314 mg, 4.79 mmol) in H2O (2.0 mL) was added over 1 h. The reaction mixture was stirred at 0° C. for 1.5 h then at rt for 45 min. The mixture was concentrated under reduced pressure (coevaporation with toluene) then dissolved in CH2Cl2 and filtered. The filtrate was concentrated under reduced pressure to give the title compound as a yellow oil. LC-MS-conditions 02: tR=0.89 min [M+H]+=281.38.

Workup

  1. waitat rt for 45 min
  2. concentrationThe mixture was concentrated under reduced pressure (coevaporation with toluene)
  3. dissolutionthen dissolved in CH2Cl2
  4. filtrationfiltered
  5. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-c48c2791002d4baea38495ae960b57fb
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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