Methyl Isocyanate → Benzaldehyde 4-methyl-2-(5-t-butyl-1,3,4-thiadiazol-2-yl)semicarbazone

HRID 615818Notes

Reaction equation

HRID 615818 reaction equation
[CH3:1][N:2]=[C:3]=[O:4].[C:5]([C:9]1[S:13][C:12]([NH:14][N:15]=[CH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)=[N:11][N:10]=1)([CH3:8])([CH3:7])[CH3:6]>C(OCC)(=O)C.C(N(CC)CC)C>[CH3:1][NH:2][C:3](=[O:4])[N:14]([C:12]1[S:13][C:9]([C:5]([CH3:8])([CH3:7])[CH3:6])=[N:10][N:11]=1)[N:15]=[CH:16][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=1

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 70487433Benzaldehyde 5-t-butyl-1,3,4-thiadiazolyl hydrazone

Product 1

HCID 53934083Benzaldehyde 4-methyl-2-(5-t-butyl-1,3,4-thiadiazol-2-yl)semicarbazoneYield 22.1%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 8857Ethyl AcetateSolvent

Procedure

Methyl isocyanate (1.88 g) was added to a stirred suspension of benzaldehyde 5-t-butyl-1,3,4-thiadiazolyl hydrazone (7.8 g) in ethyl acetate (60 ml). Triethylamine (3 drops) was then added and the mixture was stirred for 2 hours. The solvent was evaporated to give a white solid, purified by chromatography. The pure fractions were combined and recrystallised from a mixture of ethyl acetate and hexane to give benzaldehyde 4-methyl-2-(5-t-butyl-1,3,4-thiadiazol-2-yl)semicarbazone (2.1 g, 22%) as a white powder, mp 115°-116° C.

Workup

  1. customThe solvent was evaporated
  2. customto give a white solid
  3. custompurified by chromatography
  4. customrecrystallised from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-35ad602451fe48829f4634441d5927f9
Source dataset
uspto-grants-1985_02
Patent number
US04501605

Reaction notes

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