2-Isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazole → 3-[1-Methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

HRID 972404Notes

Reaction equation

HRID 972404 reaction equation
[F:1][C:2]([C:5]1[S:9][C:8]([N:10]=[C:11]=[O:12])=[N:7][N:6]=1)([F:4])[F:3].[CH3:13][NH:14][CH2:15][CH2:16][CH:17]=[O:18]>C1C=CC=CC=1>[CH3:13][N:14]([CH2:15][CH2:16][CH:17]=[O:18])[C:11]([NH:10][C:8]1[S:9][C:5]([C:2]([F:3])([F:1])[F:4])=[N:6][N:7]=1)=[O:12]

Participants

4

Reactant 2

HCID 131418952-Isocyanato-5-(trifluoromethyl)-1,3,4-thiadiazoleHCID 212547783-(Methylamino)propanal

Product 1

HCID 214000943-[1-Methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent2×

Procedure

A mixture of 5 trifluoromethyl-1,3,4-thiadiazol-2-yl isocyanate dimer (9.5 grams), the dimethyl acetal of 3-methylaminopropionaldehyde (5.8 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. This product is recrystallized to yield the desired product the dimethyl acetal of 3-[1-methyl-3-(5-trifluoromethyl-1,3,4-thiadiazol-2-yl)ureido]propionaldehyde.

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. customThis product is recrystallized

Sources & evidence

ORD record
ord-9cdbee84d2c24c8ca2e803f33f5f9cab
Source dataset
uspto-grants-1977_10
Patent number
US04053298

Reaction notes

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