18-Crown-6 → 2-(1-Azidoethyl)-5-(4-chlorophenyl)-4-methyloxazole

HRID 57382Notes

Reaction equation

HRID 57382 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].O1CCOCCOCCOCCOCCOCC1.Cl[CH:24]([C:26]1[O:27][C:28]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[C:29]([CH3:31])[N:30]=1)[CH3:25]>C(#N)C>[N:1]([CH:24]([C:26]1[O:27][C:28]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)=[C:29]([CH3:31])[N:30]=1)[CH3:25])=[N+:2]=[N-:3]

Participants

5

Reactant 3

HCID 2855718-Crown-6HCID 33557Sodium AzideHCID 431442571152541-88-2

Product 1

HCID 904151212-(1-Azidoethyl)-5-(4-chlorophenyl)-4-methyloxazoleYield 99.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

Sodium azide (635 mg, 9.760 mmol) and a catalytic amount of 1,4,7,10,13,16-hexaoxacyclooctadecane was added to a solution of 2-(1-chloroethyl)-5-(4-chlorophenyl)-4-methyloxazole (250 mg, 0.976 mmol) in acetonitrile (10 ml) and reluxed at 80° C. for 3 hours. The reaction was concentrated in vacuo. Flash column chromatography (silica, 40 g) eluting with 0-5% EtOAc/DCM provided the title compound (254 mg, clear oil). HRMS(C) tR=1.52 min; MS m/z 262.0621

Workup

  1. concentrationThe reaction was concentrated in vacuo
  2. washFlash column chromatography (silica, 40 g) eluting with 0-5% EtOAc/DCM

Sources & evidence

ORD record
ord-41795b4308c54f0dbd0a0eb1fc1abe24
Source dataset
uspto-grants-2016_09
Patent number
US09434719B2

Reaction notes

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