Azetidine → HCID 53467570, compound

HRID 1055252Notes

Reaction equation

HRID 1055252 reaction equation
[NH:1]1[CH2:4][CH2:3][CH2:2]1.[CH2:5]=[C:6]1[O:10][C:8](=[O:9])[CH2:7]1>O1CCCC1>[N:1]1([C:8](=[O:9])[CH2:7][C:6](=[O:10])[CH3:5])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 10422AzetidineHCID 12661Diketene

Product 1

HCID 53467570HCID 53467570, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 18.00 g (0.31 mol) azetidine in 50 ml tetrahydrofuran was added dropwise to a solution of 25.00 g of diketene (0.30 mol) in 200 ml tetrahydrofuran at −5 to 0° C. After 1 h stirring at 0° C. no more starting material was detected by thin layer chromatography. The reaction mixture was evaporated and the residue is recrystallized from 100 ml of ethyl acetate. This gave 26.45 g (0.19 mol, 63% yield) of a white solid.

Workup

  1. customThe reaction mixture was evaporated
  2. customthe residue is recrystallized from 100 ml of ethyl acetate

Sources & evidence

ORD record
ord-ee3fb2fdb7004a8086d4a6d0e2978408
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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