Hydrogen Bromide → HCID 15027123, compound

HRID 326514Notes

Reaction equation

HRID 326514 reaction equation
[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=3)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].Br.I.O>C(O)(=O)C>[CH2:1]([C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:20]3[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=3)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8]

Participants

6

Reactant 4

HCID 260Hydrogen BromideHCID 962WaterHCID 24841Hydrogen iodideHCID 15027122HCID 15027122, compound

Product 1

HCID 15027123HCID 15027123, compoundYield 22.8%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

In a 200 ml-round-bottomed flask, 8.20 g (21.6 mM) of 2-(4-octylphenyl)-5-(4-methoxyphenyl)thiazole, 80 ml of a solution of 25%-hydrogen bromide in acetic acid and 3 ml of 57%-hydroiodic acid were placed, followed by heat-stirring for 20 hours at 100° C. After the reaction, the reaction mixture was poured into 200 ml of water, followed by extraction with chloroform. The organic layer was washed with water and dried with anhydrous sodium sulfate, followed by distilling-off of the solvent under reduced pressure. The residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1) to obtain 1.80 g of 2-(4-octylphenyl)-5-(4-hydroxyphenyl)thiazole (Yield: 22.8%).

Workup

  1. customAfter the reaction
  2. extractionfollowed by extraction with chloroform
  3. washThe organic layer was washed with water
  4. dry with materialdried with anhydrous sodium sulfate
  5. customThe residue was purified by silica gel column chromatography (eluent: chloroform/ethyl acetate=20/1)

Sources & evidence

ORD record
ord-141d787b1f784faa94d2aab60d64b5df
Source dataset
uspto-grants-1993_12
Patent number
US05269964

Reaction notes

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