Ethylene Glycol → HCID 14673963, compound

HRID 1199414Notes

Reaction equation

HRID 1199414 reaction equation
[CH3:1][C:2]1([CH3:23])[O:15][C:6]2=[CH:7][C:8]3[C:9]([CH:14]=[C:5]2[CH:4]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:22])=[N:10][O:11][N+:12]=3[O-].C(O)CO.[N-]=[N+]=[N-].[Na+]>O>[CH3:1][C:2]1([CH3:23])[O:15][C:6]2=[CH:7][C:8]3[C:9]([CH:14]=[C:5]2[CH:4]([N:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]1[OH:22])=[N:10][O:11][N:12]=3

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 33557Sodium AzideHCID 14673958HCID 14673958, compound

Product 1

HCID 14673963HCID 14673963, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 297 mg (0.93 m mol) of 7,8-dihydro-6,6-dimethyl-7-hydroxy-8-(1-piperidinyl)-6H-pyrano [2,3-f] benzo-2,1,3-oxadiazole 3-oxide, 6 ml of ethylene glycol and 60 mg (0.93 m mol) of NaN3 was heated to 140° C. and reacted for 1.2 hours. After cooling, the reaction solution was poured into water and extracted thrice with chloroform. After the combined chloroform layer was dried over anhydrous sodium sulfate, the solvent was distilled off. The residue was subjected to a silica gel column chromatography using a developing solvent of ethyl acetate-hexane (1:3 (v/v)) to obtain 84 mg (yield: 30%) of the intended compound as oil. A part of the obtained compound was dissolved in ethanol-ethyl ether and added with HCl--EtOH to obtain the hydrochloride of the intended compound as pale yellow crystals.

Workup

  1. customreacted for 1.2 hours
  2. temperatureAfter cooling
  3. extractionextracted thrice with chloroform
  4. dry with materialAfter the combined chloroform layer was dried over anhydrous sodium sulfate
  5. distillationthe solvent was distilled off

Sources & evidence

ORD record
ord-4d6e7f4a7ad842a1bf534e93a227b362
Source dataset
uspto-grants-1990_02
Patent number
US04900752

Reaction notes

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