2-t-Butyl-1,3,4-thiadiazol-5-yl Isocyanate → 2-[1-Allyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]-3-methoxypropionaldehyde

HRID 2083586Notes

Reaction equation

HRID 2083586 reaction equation
[C:1]([C:5]1[S:9][C:8]([N:10]=[C:11]=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH2:13]([NH:16][CH:17]([CH2:20][O:21][CH3:22])[CH:18]=[O:19])[CH:14]=[CH2:15]>C1C=CC=CC=1>[CH2:13]([N:16]([CH:17]([CH2:20][O:21][CH3:22])[CH:18]=[O:19])[C:11]([NH:10][C:8]1[S:9][C:5]([C:1]([CH3:4])([CH3:2])[CH3:3])=[N:6][N:7]=1)=[O:12])[CH:14]=[CH2:15]

Participants

4

Reactant 2

HCID 64524562-t-Butyl-1,3,4-thiadiazol-5-yl IsocyanateHCID 203570002-Allylamino-3-methoxypropionaldehyde

Product 1

HCID 203570342-[1-Allyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]-3-methoxypropionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-t-Butyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-allylamino-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-allyl-3-(5-t-butyl-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-f2cd9699cc514b21a2244a06b3d03303
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

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