2-Ethylamino-3-methoxypropionaldehyde → 2-[1-Ethyl-3-(5-methylthio-1,3,4-thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

HRID 2083594Notes

Reaction equation

HRID 2083594 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([N:8]=[C:9]=[O:10])=[N:5][N:4]=1.[CH2:11]([NH:13][CH:14]([CH2:17][O:18][CH3:19])[CH:15]=[O:16])[CH3:12]>C1C=CC=CC=1>[CH2:11]([N:13]([CH:14]([CH2:17][O:18][CH3:19])[CH:15]=[O:16])[C:9]([NH:8][C:6]1[S:7][C:3]([S:2][CH3:1])=[N:4][N:5]=1)=[O:10])[CH3:12]

Participants

4

Reactant 2

HCID 203570262-Ethylamino-3-methoxypropionaldehydeHCID 537505795-Methylthio-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203570042-[1-Ethyl-3-(5-methylthio-1,3,4-thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Methylthio-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-ethylamino-3-methoxypropionaldehyde (0.1 mole) and benzene (60 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer, thermometer and reflux condenser. The reaction mixture is heated at reflux for a period of about 30 minutes. After this time the mixture is stripped of benzene under reduced pressure to yield a solid product as the residue. This residue is then recrystallized to yield the desired product the dimethyl acetal of 2-[1-ethyl-3-(5-methylthio-1,3,4-thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturethermometer and reflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 30 minutes
  5. customto yield a solid product as the residue
  6. customThis residue is then recrystallized

Sources & evidence

ORD record
ord-731ced5cc6e748149a713479162cbebf
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

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