2-Butylamino-3-methoxypropionaldehyde → 2-[1-Butyl-3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)ureido]-3-methoxypropionaldehyde

HRID 2083600Notes

Reaction equation

HRID 2083600 reaction equation
[CH3:1][S:2]([C:4]1[S:8][C:7]([N:9]=[C:10]=[O:11])=[N:6][N:5]=1)=[O:3].[CH2:12]([NH:16][CH:17]([CH2:20][O:21][CH3:22])[CH:18]=[O:19])[CH2:13][CH2:14][CH3:15]>C1C=CC=CC=1>[CH2:12]([N:16]([CH:17]([CH2:20][O:21][CH3:22])[CH:18]=[O:19])[C:10]([NH:9][C:7]1[S:8][C:4]([S:2]([CH3:1])=[O:3])=[N:5][N:6]=1)=[O:11])[CH2:13][CH2:14][CH3:15]

Participants

4

Reactant 2

HCID 203570102-Butylamino-3-methoxypropionaldehydeHCID 540842185-Methylsulfinyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203570452-[1-Butyl-3-(5-methylsulfinyl-1,3,4-thiadiazol-2-yl)ureido]-3-methoxypropionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Methylsulfinyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-butylamino-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-butyl-3-(5-methylsulfinyl-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-667da1169559438da534ae192b4c19aa
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

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