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

HRID 972538Notes

Reaction equation

HRID 972538 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.[CH2:12]([CH:15]([NH2:18])C=O)[C:13]#C.C([O:22][CH2:23][CH3:24])(=O)C>>[CH2:15]([N:18]([CH2:24][CH:23]=[O:22])[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:12]#[CH:13]

Participants

4

Reactant 3

HCID 8857Ethyl AcetateHCID 539755145-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanateHCID 552856542-Propargyl-aminoacetaldehyde

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-propargyl-aminoacetaldehyde (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-14c3d97f4c8a4b8ab6416fbf396b325e
Source dataset
uspto-grants-1977_10
Patent number
US04053480

Reaction notes

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