Benzene → 2-[1-Methyl-3-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

HRID 596733Notes

Reaction equation

HRID 596733 reaction equation
[CH:1]1([C:7]2[S:11][C:10]([N:12]=[C:13]=[O:14])=[N:9][N:8]=2)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.C[CH:16]([NH2:19])[CH:17]=[O:18].[CH:20]1C=CC=CC=1>>[CH3:20][N:19]([CH2:16][CH:17]=[O:18])[C:13]([NH:12][C:10]1[S:11][C:7]([CH:1]2[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]2)=[N:8][N:9]=1)=[O:14]

Participants

4

Reactant 3

HCID 241Benzene2×HCID 188982AlaninalHCID 539244442-Cyclohexyl-5-isocyanato-1,3,4-thiadiazole

Product 1

HCID 203927082-[1-Methyl-3-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde

Procedure

A mixture of 5-cyclohexyl-1,3,4-thiadiazol-2-yl isocyanate dimer (12 grams), the dimethyl acetal of 2-methyl-aminoacetaldehyde (6.9 grams) 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 from methanol to yield the desired product the dimethyl acetal of 2-[1-methyl-3-(5-cyclohexyl-1,3,4-thiadiazol-2-yl)ureido]acetaldehyde having a melt point of 133° to 134° C.

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 from methanol

Sources & evidence

ORD record
ord-8c33973b3c0e4f719861ec47280035a7
Source dataset
uspto-grants-1977_03
Patent number
US04012223

Reaction notes

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