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

HRID 436834Notes

Reaction equation

HRID 436834 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][CH2:17][CH:18]=[O:19])[CH:14]=[CH2:15]>C1C=CC=CC=1>[CH2:13]([N:16]([CH2:17][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 205484762-Allylaminoacetaldehyde

Product 1

HCID 203246432-[1-Allyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer (8.7 grams), the diethyl acetal of 2-allylaminoacetaldehyde (8.0 grams) and benzene (50 ml) was charged into a glass reaction flask equipped with a mechanical stirrer and thermometer. The reaction mixture was then warmed with stirring until the reactants dissolved. After this time the reaction mixture was stripped of benzene to yield an oil. This oil was dissolved in an ether-pentane mixture and was treated with diatomaceous earth and filtered. The filtrate was then stripped of solvent to yield the desired product the diethyl acetal of 2-[1-allyl-3-(5-t-butyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde as a dark red oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperatureThe reaction mixture was then warmed
  3. dissolutiondissolved
  4. customto yield an oil
  5. additionwas treated with diatomaceous earth
  6. filtrationfiltered

Sources & evidence

ORD record
ord-472293e49f084c759e4e949c2fa80ab3
Source dataset
uspto-grants-1977_06
Patent number
US04028375

Reaction notes

Loading…