Water → HCID 4308986, compound

HRID 1374150Notes

Reaction equation

HRID 1374150 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].Br[C:6]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][CH2:7]1.O.C(OCC)C>CS(C)=O>[N:1]([C:6]1([C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH2:9][CH2:8][CH2:7]1)=[N+:2]=[N-:3]

Participants

6

Reactant 4

HCID 962WaterHCID 3283Diethyl EtherHCID 33557Sodium AzideHCID 97595Ethyl 1-bromocyclobutanecarboxylate

Product 1

HCID 4308986HCID 4308986, compoundYield 97.7%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Conditions

Temperature
40 °C

Procedure

Sodium azide (3.14 g, 48.3 mmol) was partially dissolved in dry DMSO (50 mL), under nitrogen at ambient temperature. Ethyl 1-bromocyclobutanecarboxylate (3.91 mL, 24.2 mmol, Aldrich) was then added via syringe. After heating to 40° C. for 7 hours, the homogenous solution was allowed to cool to ambient temperature and stirring was continued overnight. The reaction mixture was then poured into water (700 mL), along with diethyl ether (200 mL). The ether layer was washed three times with half brine and then once with brine. The organic layer was dried over sodium sulfate, filtered and then evaporated under reduced pressure to provide ethyl 1-azidocyclobutanecarboxylate (4.00 g) as a clear oil.

Workup

  1. temperatureto cool to ambient temperature
  2. washThe ether layer was washed three times with half brine
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. filtrationfiltered
  5. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-d955b24c9b4c45bd8c6e11b58a5c14e1
Source dataset
uspto-grants-2007_01
Patent number
US07163951B2

Reaction notes

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