Diketene → HCID 53467572, compound

HRID 1055251Notes

Reaction equation

HRID 1055251 reaction equation
[CH:1]1([NH2:5])[CH2:4][CH2:3][CH2:2]1.[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>O1CCCC1>[CH:1]1([NH:5][C:9](=[O:10])[CH2:8][C:7](=[O:11])[CH3:6])[CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 75645Cyclobutylamine

Product 1

HCID 53467572HCID 53467572, compoundYield 61.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 20.00 g (0.28 mol) cyclobutylamine in 50 ml tetrahydrofuran was added dropwise to a solution of 22.00 g of diketene (0.26 mole) 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 24.60 g (0.16 mol, 61% 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-2457bed0d3394319b768db3653c77b8a
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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