Water → HCID 13173180, compound

HRID 980359Notes

Reaction equation

HRID 980359 reaction equation
[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([CH:23]=2)[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:4])([CH3:3])[CH3:2].[S-:24][C:25]#[N:26].[Na+].BrBr.O>C(O)(=O)C>[C:1]([C:5]1[CH:6]=[C:7]([C:16]2[N:17]=[C:18]3[N:22]([C:23]=2[S:24][C:25]#[N:26])[CH2:21][CH2:20][S:19]3)[CH:8]=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[C:10]=1[OH:11])([CH3:2])([CH3:3])[CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24408BromineHCID 516871Sodium thiocyanateHCID 13173170HCID 13173170, compound

Product 1

HCID 13173180HCID 13173180, compoundYield 37.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

In 10 ml of acetic acid was dissolved 1.35 g of 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-2,3-dihydroimidazo[2,1-b]thiazole and after adding thereto 0.64 g of sodium thiocyanate, 0.7 g of bromine was added dropwise to the solution under ice-cooling. After performing the reaction for one hour at room temperature, 30 ml of water was added to the reaction mixture to precipitate crystals, which were recovered by filtration. The crystals were added to a mixture of 20 ml of chloroform and 10 ml of an aqueous 10% potassium carbonate solution followed by stirring. The chloroform layer thus formed was dried and concentrated, and the residue thus formed was purified by silica gel column chromatography using chloroform as the eluent and further recrystallized from ethanol to provide 0.6 g 6-(3,5-di-tert-butyl-4-hydroxyphenyl)-5-thiocyanato-2,3-dihydroimidazo[2,1-b]thiazole.

Workup

  1. additionafter adding
  2. temperaturecooling
  3. customthe reaction for one hour at room temperature
  4. customto precipitate crystals, which
  5. filtrationwere recovered by filtration
  6. additionThe crystals were added to a mixture of 20 ml of chloroform and 10 ml of an aqueous 10% potassium carbonate solution
  7. customThe chloroform layer thus formed
  8. customwas dried
  9. concentrationconcentrated
  10. customthe residue thus formed
  11. customwas purified by silica gel column chromatography
  12. customfurther recrystallized from ethanol

Sources & evidence

ORD record
ord-466598532c3a4e849396de18d4333139
Source dataset
uspto-grants-1987_01
Patent number
US04636516

Reaction notes

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