3-(Methylamino)propanal → 3-[1-Methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

HRID 435520Notes

Reaction equation

HRID 435520 reaction equation
[CH3:1][C:2]1[S:6][C:5]([N:7]=[C:8]=[O:9])=[N:4][N:3]=1.[CH3:10][NH:11][CH2:12][CH2:13][CH:14]=[O:15]>C1C=CC=CC=1>[CH3:10][N:11]([CH2:12][CH2:13][CH:14]=[O:15])[C:8]([NH:7][C:5]1[S:6][C:2]([CH3:1])=[N:3][N:4]=1)=[O:9]

Participants

4

Reactant 2

HCID 212547783-(Methylamino)propanalHCID 542820282-Isocyanato-5-methyl-1,3,4-thiadiazole

Product 1

HCID 214001113-[1-Methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-methyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 3-methylaminopropionaldehyde (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 dimethyl acetal of 3-[1-methyl-3-(5-methyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde.

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-d62c315cdbe9401799dd98605cf30d62
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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