Nitrogen → HCID 86664913, compound

HRID 1189403Notes

Reaction equation

HRID 1189403 reaction equation
N#N.[C:3]([C:6]1[S:10][C:9]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17](Cl)=[O:18])[N:16]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH3:20][C:21]1([C:26]2[S:30][C:29]([CH2:31][C:32]3[O:33][CH:34]=[C:35]([C:37](Cl)=[O:38])[N:36]=3)=[CH:28][CH:27]=2)[O:25][CH2:24][CH2:23][O:22]1.[N-:40]=[N+:41]=[N-:42].[Na+]>CC(C)=O.O>[C:3]([C:6]1[S:10][C:9]([CH2:11][C:12]2[O:13][CH:14]=[C:15]([C:17]([N:40]=[N+:41]=[N-:42])=[O:18])[N:16]=2)=[CH:8][CH:7]=1)(=[O:5])[CH3:4].[CH3:20][C:21]1([C:26]2[S:30][C:29]([CH2:31][C:32]3[O:33][CH:34]=[C:35]([C:37]([N:40]=[N+:41]=[N-:42])=[O:38])[N:36]=3)=[CH:28][CH:27]=2)[O:25][CH2:24][CH2:23][O:22]1

Participants

8

Reactant 4

HCID 947NitrogenHCID 33557Sodium AzideHCID 86664915HCID 86664915, compoundHCID 866649162-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carbonyl chloride

Product 2

HCID 86664913HCID 86664913, compoundHCID 866649142-[5-(2-Methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-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), a solution of this crude mixture of 2-(5-acetyl-thiophen-2-ylmethyl)-oxazole-4-carbonyl chloride and 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carbonyl chloride in dry acetone (12.0 mL) was cooled to 0° C. and a solution of sodium azide (262 mg, 3.98 mmol) in H2O (1.4 mL) was added over 1 h. The reaction mixture was stirred at 0° C. for 45 min. The mixture was concentrated under reduced pressure (co-evaporation with toluene) then dissolved in CH2Cl2 and filtered. The filtrated was concentrated under reduced pressure to give the title compound (LC-MS-conditions 01: tR=0.85 min, [M+H]+=276.91) along with 2-[5-(2-methyl-[1,3]dioxolan-2-yl)-thiophen-2-ylmethyl]-oxazole-4-carbonyl azide (LC-MS-conditions 01: tR=0.91 min, [M+H]+=320.92) as a brown solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure (co-evaporation with toluene)
  2. dissolutionthen dissolved in CH2Cl2
  3. filtrationfiltered
  4. concentrationThe filtrated was concentrated under reduced pressure

Sources & evidence

ORD record
ord-bacd367fd2754ddabc7bf3fd4606ec8d
Source dataset
uspto-grants-2014_03
Patent number
US08674111B2

Reaction notes

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