2-Propargylamino-3-methoxypropionaldehyde → 2-[1-Propargyl-3-(5-hexyl-1,3,4thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

HRID 2083588Notes

Reaction equation

HRID 2083588 reaction equation
[CH2:1]([C:7]1[S:11][C:10]([N:12]=[C:13]=[O:14])=[N:9][N:8]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[CH2:15]([NH:18][CH:19]([CH2:22][O:23][CH3:24])[CH:20]=[O:21])[C:16]#[CH:17]>C1C=CC=CC=1>[CH2:15]([N:18]([CH:19]([CH2:22][O:23][CH3:24])[CH:20]=[O:21])[C:13]([NH:12][C:10]1[S:11][C:7]([CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH3:6])=[N:8][N:9]=1)=[O:14])[C:16]#[CH:17]

Participants

4

Reactant 2

HCID 203570222-Propargylamino-3-methoxypropionaldehydeHCID 539065275-Hexyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 203570122-[1-Propargyl-3-(5-hexyl-1,3,4thiadiazol-2-yl)-ureido]-3-methoxypropionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

5-Hexyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-propargylamino-3-methoxy-propionaldehyde (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-propargyl-3-(5-hexyl-1,3,4thiadiazol-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-10c52cf38fd14c07830f6335c54e0e41
Source dataset
uspto-grants-1978_04
Patent number
US04086238

Reaction notes

Loading…