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

HRID 1415361Notes

Reaction equation

HRID 1415361 reaction equation
[CH:1]1([C:7]2[S:11][C:10]([N:12]=[C:13]=[O:14])=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[CH2:15]([NH:18][CH2:19][CH2:20][CH:21]=[O:22])[CH:16]=[CH2:17]>C1C=CC=CC=1>[CH2:15]([N:18]([CH2:19][CH2:20][CH:21]=[O:22])[C:13]([NH:12][C:10]1[S:11][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:8][N:9]=1)=[O:14])[CH:16]=[CH2:17]

Participants

4

Reactant 2

HCID 214000913-AllylaminopropionaldehydeHCID 539244442-Cyclohexyl-5-isocyanato-1,3,4-thiadiazole

Product 1

HCID 214819043-[1-Allyl-3-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-cyclohexyl-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 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-allyl-3-(5-cyclohexyl-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-abf99bdc62cc4d09870bee5fea266acf
Source dataset
uspto-grants-1977_01
Patent number
US04004912

Reaction notes

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