3-But-3-enylaminopropionaldehyde → 3-[1-But-3-enyl-3-(5-methoxy-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

HRID 435541Notes

Reaction equation

HRID 435541 reaction equation
[CH3:1][O:2][C:3]1[S:7][C:6]([N:8]=[C:9]=[O:10])=[N:5][N:4]=1.[CH2:11]([NH:15][CH2:16][CH2:17][CH:18]=[O:19])[CH2:12][CH:13]=[CH2:14]>C1C=CC=CC=1>[CH2:11]([N:15]([CH2:16][CH2:17][CH:18]=[O:19])[C:9]([NH:8][C:6]1[S:7][C:3]([O:2][CH3:1])=[N:4][N:5]=1)=[O:10])[CH2:12][CH:13]=[CH2:14]

Participants

4

Reactant 2

HCID 214001083-But-3-enylaminopropionaldehydeHCID 451234665-Methoxy-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 214001093-[1-But-3-enyl-3-(5-methoxy-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-methoxy-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the diethyl acetyl of 3-but-3-enylaminopropionaldehyde (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 the desired product the diethyl acetal of 3-[1-but-3-enyl-3-(5-methoxy-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

Sources & evidence

ORD record
ord-f6d6719c689449f3b10029134086f579
Source dataset
uspto-grants-1977_02
Patent number
US04006009

Reaction notes

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