HCID 20324635, compound → HCID 20324617, compound

HRID 436845Notes

Reaction equation

HRID 436845 reaction equation
[CH3:1][S:2]([C:5]1[S:9][C:8]([N:10]=[C:11]=[O:12])=[N:7][N:6]=1)(=[O:4])=[O:3].[CH3:13][C:14]([NH:18][CH2:19][CH:20]=[O:21])([CH3:17])[C:15]#[CH:16]>C1C=CC=CC=1>[CH3:13][C:14]([N:18]([CH2:19][CH:20]=[O:21])[C:11]([NH:10][C:8]1[S:9][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[N:6][N:7]=1)=[O:12])([CH3:17])[C:15]#[CH:16]

Participants

4

Reactant 2

HCID 20324635HCID 20324635, compoundHCID 542537365-Methylsulfonyl-1,3,4-thiadiazol-2-yl isocyanate

Product 1

HCID 20324617HCID 20324617, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5-methylsulfonyl-1,3,4-thiadiazol-2-yl isocyanate dimer (0.05 mole), the diethyl acetal of 2-(1,1-dimethylprop-2-ynylamino)acetaldehyde (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 diethyl acetal of 2-[1-(1,1-dimethylprop-2-ynyl)-3-(5-methylsulfonyl-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-be12d50e7c8346b3a1cf3abbe2a05a36
Source dataset
uspto-grants-1977_06
Patent number
US04028375

Reaction notes

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