Thiosemicarbazide → HCID 136018200, compound

HRID 486101Notes

Reaction equation

HRID 486101 reaction equation
[CH3:1][C:2]([C:5]1[CH:6]=[C:7]([CH:16]=[C:17]2[S:21][C:20](SC)=[N:19][C:18]2=[O:24])[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])[CH3:3].[NH2:25][NH:26][C:27]([NH2:29])=[S:28]>C(O)C>[CH3:13][C:12]([C:9]1[CH:8]=[C:7]([CH:16]=[C:17]2[S:21][C:20](=[N:25][NH:26][C:27](=[S:28])[NH2:29])[NH:19][C:18]2=[O:24])[CH:6]=[C:5]([C:2]([CH3:3])([CH3:4])[CH3:1])[C:10]=1[OH:11])([CH3:14])[CH3:15]

Participants

4

Reactant 2

HCID 2723789ThiosemicarbazideHCID 53858627HCID 53858627, compound

Product 1

HCID 136018200HCID 136018200, compoundYield 84.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 5-[(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-2-(methylthio)-4(5H)-thiazolone (6.13 g, 0.0169 mole) and thiosemicarbazide (1.53 g, 0.0169 mole) in ethanol (300 mL) is refluxed with stirring for 7 hours. After standing overnight at room temperature, the product is separated by filtration, washed with ethanol to give 5.78 g of a solid. It is recrystallized from DMF-methanol to give 3.4 g (47%) of pure 2-[5-[[3,5-Bis(1,1-dimethylethyl)-4-hydroxyphenyl]methylene]-4-oxo-2-thiazolidinylidene]hydrazinecarbothiamide, (Z)-, mp 200°-202° C.

Workup

  1. temperatureis refluxed
  2. waitAfter standing overnight at room temperature
  3. customthe product is separated by filtration
  4. washwashed with ethanol

Sources & evidence

ORD record
ord-7b2c72583734437f8064854dda85fe50
Source dataset
uspto-grants-1994_03
Patent number
US05290800

Reaction notes

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