3-Allylaminopropionaldehyde → 3-[1-Allyl-3-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

HRID 1605878Notes

Reaction equation

HRID 1605878 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([N:10]=[C:11]=[O:12])=[N:7][N:6]=1)(=[O:4])=[O:3].[CH2:13]([NH:16][CH2:17][CH2:18][CH:19]=[O:20])[CH:14]=[CH2:15]>C1C=CC=CC=1>[CH2:13]([N:16]([CH2:17][CH2:18][CH:19]=[O:20])[C:11]([NH:10][C:8]1[S:9][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:6][N:7]=1)=[O:12])[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 214000913-AllylaminopropionaldehydeHCID 542537365-Methylsulfonyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 214000773-[1-Allyl-3-(5-methylsulfonyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5-methylsulfonyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 3-allylaminopropionaldehyde (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 benzeneunder 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-allyl-3-(5-methylsulfonyl-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-3b7e32d6c9094d60be5bbc4db3734dc8
Source dataset
uspto-grants-1976_04
Patent number
US03951976

Reaction notes

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