2-Pentylamino-3-methoxypropionaldehyde → 2-[1-Pentyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

HRID 2083603Notes

Reaction equation

HRID 2083603 reaction equation
[CH:1]1([C:4]2[S:8][C:7]([N:9]=[C:10]=[O:11])=[N:6][N:5]=2)[CH2:3][CH2:2]1.[CH2:12]([NH:17][CH:18]([CH2:21][O:22][CH3:23])[CH:19]=[O:20])[CH2:13][CH2:14][CH2:15][CH3:16]>C1C=CC=CC=1>[CH2:12]([N:17]([CH:18]([CH2:21][O:22][CH3:23])[CH:19]=[O:20])[C:10]([NH:9][C:7]1[S:8][C:4]([CH:1]2[CH2:3][CH2:2]2)=[N:5][N:6]=1)=[O:11])[CH2:13][CH2:14][CH2:15][CH3:16]

Participants

4

Reactant 2

HCID 203570052-Pentylamino-3-methoxypropionaldehydeHCID 539755145-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203570062-[1-Pentyl-3-(5-cyclopropyl-1,3,4-thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Cyclopropyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-pentylamino-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-pentyl-3-(5-cyclopropyl-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-6669e1ce505342798764975e9eb9a742
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

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