Phenyltrimethylammonium bromide dibromide → HCID 58451404, compound

HRID 456028Notes

Reaction equation

HRID 456028 reaction equation
[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:18])[CH3:17])[N:15]=1)([CH3:9])[CH3:8])([CH3:4])([CH3:3])[CH3:2].[Br-:20].[Br-].[Br-].C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1.C1([N+](C)(C)C)C=CC=CC=1>O1CCCC1>[C:1]([O:5][C:6](=[O:19])[C:7]([S:10][C:11]1[S:12][CH:13]=[C:14]([C:16](=[O:18])[CH2:17][Br:20])[N:15]=1)([CH3:9])[CH3:8])([CH3:2])([CH3:3])[CH3:4]

Participants

4

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 58451405HCID 58451405, compound

Product 1

HCID 58451404HCID 58451404, compoundYield 96%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-{[4-Acetyl-1,3-thiazol-2-yl]thio}-2-methylpropionic acid tert-butyl ester (15.90 g) obtained in Example 8 was dissolved in tetrahydrofuran (150 mL), phenyltrimethylammonium tribromide (21.81 g) was added by small portions over 15 min, and the mixture was stirred at room temperature overnight. The precipitated solid was filtered off, the solvent was evaporated, and the residue was dissolved in ethyl acetate (200 mL). The solution was washed successively with water and saturated aqueous sodium chloride solution (each 100 mL) and dried over anhydrous sodium sulfate. The solvent was evaporated and the obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 3 L, elution solvent: hexane/ethyl acetate-90/10-50/50, performed in 5 times) to give the title compound (12.28 g).

Workup

  1. filtrationThe precipitated solid was filtered off
  2. customthe solvent was evaporated
  3. dissolutionthe residue was dissolved in ethyl acetate (200 mL)
  4. washThe solution was washed successively with water and saturated aqueous sodium chloride solution (each 100 mL) and
  5. dry with materialdried over anhydrous sodium sulfate
  6. customThe solvent was evaporated
  7. customthe obtained residue was purified by column chromatography (Yamazen HI-FLASH™ COLUMN size 3 L, elution solvent: hexane/ethyl acetate-90/10-50/50, performed in 5 times)

Sources & evidence

ORD record
ord-31cefc5d6fb84bfeae618547d3709a64
Source dataset
uspto-grants-2013_07
Patent number
US08497382B2

Reaction notes

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