2-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-one → 2H-Imidazo(2,1-b)(1,3,4)thiadiazin-6(7H)-one, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-, hydrobromide

HRID 329386

Reaction equation

HRID 329386 reaction equation
[Br:1][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.[NH2:20][N:21]1[C:25](=[O:26])[CH2:24][NH:23][C:22]1=[S:27]>>[BrH:1].[C:11]([C:9]1[CH:10]=[C:5]([C:3]2[CH2:2][S:27][C:22]3=[N:23][CH2:24][C:25](=[O:26])[N:21]3[N:20]=2)[CH:6]=[C:7]([C:16]([CH3:19])([CH3:18])[CH3:17])[C:8]=1[OH:15])([CH3:14])([CH3:13])[CH3:12]

Participants

3

Reactant 2

HCID 6161612-Bromo-1-[3,5-di(tert-butyl)-4-hydroxyphenyl]ethan-1-oneHCID 142110443-Amino-2-sulfanylideneimidazolidin-4-one

Product 1

HCID 30883862H-Imidazo(2,1-b)(1,3,4)thiadiazin-6(7H)-one, 3-(3,5-bis(1,1-dimethylethyl)-4-hydroxyphenyl)-, hydrobromide

Procedure

34.4 g (0.11 mol) of 2-bromo-1-(3,5-di-tert.butyl-4-hydroxyphenyl)-ethanone from Example 1(a) and 13.8 g (0.11 mol) of 1-amino-2-thioxo-5-imidazolidinone from step (a) were heated at 90° C. for 30 minutes in 300 ml of glacial acelic acid. After cooling, the precipitate was filtered off and washed with 250 ml of ethyl acetate, and the crystals were dried in vacuo over phosphorus pentoxide.

Workup

  1. temperatureAfter cooling
  2. filtrationthe precipitate was filtered off
  3. washwashed with 250 ml of ethyl acetate
  4. dry with materialthe crystals were dried in vacuo over phosphorus pentoxide

Sources & evidence

ORD record
ord-54c15c30e1fa4ef3b2056b4250981e34
Source dataset
uspto-grants-1990_01
Patent number
US04891374

Linked notes

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