Water → HCID 54386171, compound

HRID 615819Notes

Reaction equation

HRID 615819 reaction equation
[H-].[Na+].[C:3]([C:7]1[S:11][C:10]([NH:12][N:13]=[CH:14][CH3:15])=[N:9][N:8]=1)([CH3:6])([CH3:5])[CH3:4].[CH3:16][NH:17][C:18](ON=C(C1C=CC=CC=1)C#N)=[O:19].O>C1(C)C=CC=CC=1>[CH3:16][NH:17][C:18](=[O:19])[N:12]([C:10]1[S:11][C:7]([C:3]([CH3:6])([CH3:4])[CH3:5])=[N:8][N:9]=1)[N:13]=[CH:14][CH3:15]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 2726372HCID 2726372, compoundHCID 86739933HCID 86739933, compound

Product 1

HCID 54386171HCID 54386171, compoundYield 47.3%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Sodium hydride (0.12 g) was added to a stirred solution of acetaldehyde 5-t-butyl-1,3,4-thiadiazolyl hydrazone (0.99 g) in dry toluene (25 ml), and the mixture was stirred at room temperature for 15 minutes. 2-Methylaminocarbonyloxyimino-2-phenylacetonitrile (1.01 g) was added and the mixture was stirred for a further 2 hours and poured into water (20 ml). The organic phase was separated and dried over magnesium sulphate. The drying agent was filtered off and the toluene evaporated to give a yellow oil, purified by chromatography to give acetaldehyde 4-methyl-2-(5-t-butyl-1,3,4-thiadiazol-2-yl)semicarbazone (0.6 g, 47%) as a pale yellow oil.

Workup

  1. stirringthe mixture was stirred for a further 2 hours
  2. customThe organic phase was separated
  3. dry with materialdried over magnesium sulphate
  4. filtrationThe drying agent was filtered off
  5. customthe toluene evaporated
  6. customto give a yellow oil
  7. custompurified by chromatography

Sources & evidence

ORD record
ord-50a02920726d4a2495868e678bb00f34
Source dataset
uspto-grants-1985_02
Patent number
US04501605

Reaction notes

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