2-Propargylaminoacetaldehyde → 2-[1-Propargyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

HRID 436837Notes

Reaction equation

HRID 436837 reaction equation
[CH3:1][C:2]1[S:6][C:5]([N:7]=[C:8]=[O:9])=[N:4][N:3]=1.[CH2:10]([NH:13][CH2:14][CH:15]=[O:16])[C:11]#[CH:12]>C1C=CC=CC=1>[CH2:10]([N:13]([CH2:14][CH:15]=[O:16])[C:8]([NH:7][C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)=[O:9])[C:11]#[CH:12]

Participants

4

Reactant 2

HCID 203927542-PropargylaminoacetaldehydeHCID 542820282-Isocyanato-5-methyl-1,3,4-thiadiazole

Product 1

HCID 203246142-[1-Propargyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-methyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the diethyl acetal of 2-propargylaminoacetaldehyde (0.1 mole) and benzene (60 ml) are 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 15 minutes. After this time the mixture is stripped of benzene under reduced pressure to yield a solid product as the residue. The residue is then recrystallized to yield the desired product the diethyl acetal of 2-[1-propargyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 15 minutes
  5. customto yield a solid product as the residue
  6. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-c9f9e197710f4490a781cad755b89dda
Source dataset
uspto-grants-1977_06
Patent number
US04028375

Reaction notes

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