2-(Methylamino)acetaldehyde → 2-[1-Methyl-3-(5-allyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

HRID 972543Notes

Reaction equation

HRID 972543 reaction equation
[CH2:1]([C:4]1[S:8][C:7]([N:9]=[C:10]=[O:11])=[N:6][N:5]=1)[CH:2]=[CH2:3].[CH3:12][NH:13][CH2:14][CH:15]=[O:16]>C1C=CC=CC=1>[CH3:12][N:13]([CH2:14][CH:15]=[O:16])[C:10]([NH:9][C:7]1[S:8][C:4]([CH2:1][CH:2]=[CH2:3])=[N:5][N:6]=1)=[O:11]

Participants

4

Reactant 2

HCID 133161322-(Methylamino)acetaldehydeHCID 538389725-Allyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203926832-[1-Methyl-3-(5-allyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-allyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-methylaminoacetaldehyde (0.1 mole) and benzene (60 ml) is 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 dimethyl acetal of 2-[1-methyl-3-(5-allyl-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-154d705aa3924fa2a43ae52c75460695
Source dataset
uspto-grants-1977_10
Patent number
US04053480

Reaction notes

Loading…