Nitrogen → HCID 86664918, compound

HRID 1189415Notes

Reaction equation

HRID 1189415 reaction equation
N#N.[C:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9][C:10]1[O:11][CH:12]=[C:13]([C:15](Cl)=[O:16])[N:14]=1)(=[O:5])[CH3:4].[N-:21]=[N+:22]=[N-:23].[Na+]>CC(C)=O.O>[C:3]([C:6]1[CH:7]=[C:8]([CH:18]=[CH:19][CH:20]=1)[CH2:9][C:10]1[O:11][CH:12]=[C:13]([C:15]([N:21]=[N+:22]=[N-:23])=[O:16])[N:14]=1)(=[O:5])[CH3:4]

Participants

6

Reactant 3

HCID 947NitrogenHCID 33557Sodium AzideHCID 86664917HCID 86664917, compound

Product 1

HCID 86664918HCID 86664918, compound

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), a solution of the crude 2-(3-acetyl-benzyl)-oxazole-4-carbonyl chloride in dry acetone (13.5 mL) was cooled to 0° C. and a solution of sodium azide (210 mg, 3.20 mmol) in H2O (1.7 mL) was added dropwise. The reaction mixture was stirred at 0° C. for 1 h. 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 an orange oil. LC-MS-conditions 02: tR=0.91 min [M+AcCN+H]+=312.31.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure (coevaporation with toluene)
  2. dissolutionthen dissolved in CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-ae89c5bec2f04d78b45e586007dc8ce2
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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