Ethyl Acetate → 2-[1-Propargyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

HRID 460803Notes

Reaction equation

HRID 460803 reaction equation
[CH:1]1([C:4]2[S:8][C:7]([N:9]=[C:10]=[O:11])=[N:6][N:5]=2)[CH2:3][CH2:2]1.C([O:15][CH2:16][CH3:17])(=O)C>>[CH2:4]([N:5]([CH2:17][CH:16]=[O:15])[C:10]([NH:9][C:7]1[S:8][C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][N:6]=1)=[O:11])[C:1]#[CH:2]

Participants

3

Reactant 2

HCID 8857Ethyl AcetateHCID 539755145-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203926622-[1-Propargyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Procedure

A mixture of 5-cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate dimer (7 grams), the dimethyl acetal of 2-propargylaminocetaldehyde (5 grams) and ethyl acetate (50 ml) were charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated at reflux for a period of about 2 hours. After this time the mixture is stripped of solvent under reduced pressure to yield the desired product the dimethyl acetal of 2-[1-propargyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde as an oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 2 hours

Sources & evidence

ORD record
ord-b52a84e1e06f459c87a12c6884d232f0
Source dataset
uspto-grants-1977_12
Patent number
US04061648

Reaction notes

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