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

HRID 1415352Notes

Reaction equation

HRID 1415352 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.[CH3:12][NH:13][CH2:14][CH2:15][CH:16]=[O:17]>C1C=CC=CC=1>[CH3:12][N:13]([CH2:14][CH2:15][CH:16]=[O:17])[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]

Participants

4

Reactant 2

HCID 212547783-(Methylamino)propanalHCID 539755145-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 214818963-[1-Methyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-cyclopropyl-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-cyclopropyl-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-f29be1b40b2040c0b6bdd8bcb1c5aece
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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