2-(Ethylamino)acetaldehyde → 2-[1-Ethyl-3-(5-hexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

HRID 972143Notes

Reaction equation

HRID 972143 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:17][CH2:18][CH:19]=[O:20])[CH3:16]>C1C=CC=CC=1>[CH2:15]([N:17]([CH2:18][CH:19]=[O:20])[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])[CH3:16]

Participants

4

Reactant 2

HCID 205484642-(Ethylamino)acetaldehydeHCID 539065275-Hexyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 214059022-[1-Ethyl-3-(5-hexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-hexyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the dimethyl acetal of 2-ethylaminoacetaldehyde (0.1 mole) and benzene (60 ml) are charged into a glass reaction vessel equipped with a mechanical stirrer and reflux condenser. The reaction mixture is heated at reflux for a period of about 15 minutes. After this time the mixture is stripped of benzene under reduced pressure to yield a solid product as the residue. The residue is then recrystallized to yield the desired product the dimethyl acetal of 2-[1-ethyl-3-(5-hexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde.

Workup

  1. customequipped with a mechanical stirrer
  2. temperaturereflux condenser
  3. temperatureThe reaction mixture is heated
  4. temperatureat reflux for a period of about 15 minutes
  5. customto yield a solid product as the residue
  6. customThe residue is then recrystallized

Sources & evidence

ORD record
ord-794f6a27143249adaa34e6b81e29b7a6
Source dataset
uspto-grants-1977_10
Patent number
US04052191

Reaction notes

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