2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one → Phenol, 2,6-bis(1,1-dimethylethyl)-4-(2H-imidazo(2,1-b)(1,3,4)thiadiazin-3-yl)-, hydrochloride

HRID 329385

Reaction equation

HRID 329385 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]([OH:15])=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[CH:6]=1)=O.[ClH:20].[NH2:21][N:22]1[CH:26]=[CH:25][N:24]=[C:23]1[SH:27]>C(O)C>[ClH:20].[C:16]([C:7]1[CH:6]=[C:5]([C:3]2[CH2:2][S:27][C:23]3=[N:24][CH:25]=[CH:26][N:22]3[N:21]=2)[CH:10]=[C:9]([C:11]([CH3:14])([CH3:13])[CH3:12])[C:8]=1[OH:15])([CH3:19])([CH3:18])[CH3:17]

Participants

4

Reactant 2

HCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 178479588HCID 178479588, compound

Product 1

HCID 3088381Phenol, 2,6-bis(1,1-dimethylethyl)-4-(2H-imidazo(2,1-b)(1,3,4)thiadiazin-3-yl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 18.0 g (0.055 mol) of 2-bromo-1-(3,5-ditert.butyl-4-hydroxyphenyl)-ethanone and 7.6 g (0.05 mol) of 1-amino-2-mercaptoimidazole hydrochloride from step (a) in 150 ml of ethanol was refluxed for 9 hours. The residue remaining after evaporation of the solution was rendered alkaline by means of 50 ml of 2N sodium hydroxide solution and extracted with chloroform. In order to convert the product into the hydrochloride, an equimolar amount of ethereal hydrochloric acid was added to the dried chloroform phase, and the batch of crystals produced was filtered off under suction and crystallized from ethanol.

Workup

  1. customafter evaporation of the solution
  2. extractionextracted with chloroform
  3. additionan equimolar amount of ethereal hydrochloric acid was added to the dried chloroform phase
  4. customthe batch of crystals produced
  5. filtrationwas filtered off under suction
  6. customcrystallized from ethanol

Sources & evidence

ORD record
ord-23ca300e63234258a42542ff377dfc38
Source dataset
uspto-grants-1990_01
Patent number
US04891374

Linked notes

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