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

HRID 1438680Notes

Reaction equation

HRID 1438680 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].[CH3:13][NH:14][CH2:15][CH2:16][CH:17]=[O:18]>C1C=CC=CC=1>[CH3:13][N:14]([CH2:15][CH2:16][CH:17]=[O:18])[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]

Participants

4

Reactant 2

HCID 64524562-t-Butyl-1,3,4-thiadiazol-5-yl IsocyanateHCID 212547783-(Methylamino)propanal

Product 1

HCID 214000983-[1-Methyl(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer (6 grams), the dimethyl acetal of 3-methylaminopropionaldehyde (4.0 grams) and benzene (50 ml) are charged into a glass reaction flask equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated at reflux, with stirring for a period of about 5 minutes. After this time the reaction mixture is stripped of benzene to yield a residue. The residue is then recrystallized to yield the desired product the dimethyl acetal of 3-[1-methyl-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux
  5. customto yield a residue
  6. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-779b9713dcb3453187e15ad55c756d51
Source dataset
uspto-grants-1977_11
Patent number
US04056383

Reaction notes

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