Diketene → HCID 53467574, compound

HRID 1055248Notes

Reaction equation

HRID 1055248 reaction equation
[CH:1]1([CH2:4][NH2:5])[CH2:3][CH2:2]1.[CH2:6]=[C:7]1[O:11][C:9](=[O:10])[CH2:8]1>O1CCCC1>[CH:1]1([CH2:4][NH:5][C:9](=[O:10])[CH2:8][C:7](=[O:11])[CH3:6])[CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12661DiketeneHCID 75646Cyclopropanemethanamine

Product 1

HCID 53467574HCID 53467574, compoundYield 65%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
0 °C

Procedure

A solution of 15.1 g (0.22 mol) cyclopropylmethylamine in 50 ml tetrahydrofuran was added dropwise to a solution of 17 grams of diketene (0.20 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 19.7 g (0.13 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-62dcdff3971a4afd8d6eba59586b0fc2
Source dataset
uspto-grants-2016_07
Patent number
US09394324B2

Reaction notes

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