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

HRID 1076918Notes

Reaction equation

HRID 1076918 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>C(OCC)C.CCCCC>[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

5

Reactant 3

HCID 241Benzene2×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 21877078Diethylether pentaneSolvent

Procedure

A mixture of 5-t-butyl-1,3,4-thiadiazol-2-yl isocyanate dimer (8.7 grams), the diethyl acetate of 2-allylaminoacetaldehyde (8.0 grams) and benzene (30 ml) was charged into a glass reaction flask equipped with a mechanical stirrer and reflux condenser. The reaction mixture was heated with stirring for a period of about 15 minutes. After this time the reaction mixture was stripped of benzene to yield an oil. The oil was dissolved in a diethyl ether-pentane mixture and was filtered through diatomaceous earth. The filtrate was 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 oil.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture was heated
  4. customto yield an oil
  5. filtrationwas filtered through diatomaceous earth

Sources & evidence

ORD record
ord-6c35f5b9c69f4a1491357d0ba19cf10d
Source dataset
uspto-grants-1976_05
Patent number
US03958975

Reaction notes

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