Phenyltrimethylammonium bromide dibromide → Benzyl 7-(bromoacetyl)-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl carbonate

HRID 749246Notes

Reaction equation

HRID 749246 reaction equation
[C:1](=[O:24])([O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[O:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([C:13](=[O:15])[CH3:14])=[CH:5][CH:4]=1.[Br-:25].[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>C1COCC1.O>[C:1](=[O:24])([O:2][C:3]1[C:8]2[NH:9][C:10](=[O:12])[S:11][C:7]=2[C:6]([C:13](=[O:15])[CH2:14][Br:25])=[CH:5][CH:4]=1)[O:16][CH2:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 693156917-Acetyl-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl benzyl carbonate

Product 1

HCID 86605116Benzyl 7-(bromoacetyl)-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl carbonateYield 86.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-acetyl-2-oxo-2,3-dihydro-1,3-benzothiazol-4-yl benzyl carbonate (280 mg) in dry THF (20 ml) stirring under nitrogen, was added phenyltrimethylammonium tribromide (330 mg). The mixture was heated at 80° C. for 2 h and then diluted with water, extracted with ethyl acetate, dried (MgSO4), filtered, and evaporated in vacuo. The residue was purified on a 40 g silica biotage cartridge and eluted with 20% ethyl acetate-cyclohexane to give the title compound (186 mg). LCMS RT=3.43 min.

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a 40 g silica biotage cartridge
  6. washeluted with 20% ethyl acetate-cyclohexane

Sources & evidence

ORD record
ord-8aab913c5a5445ec95abd10dfc1c3d25
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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