Phenyltrimethylammonium bromide dibromide → 4-(Benzyloxy)-7-(bromoacetyl)-1,3-benzothiazol-2(3H)-one

HRID 749241Notes

Reaction equation

HRID 749241 reaction equation
[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([O:14][CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2].[Br-:22].[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>[CH2:15]([O:14][C:7]1[C:8]2[NH:9][C:10](=[O:13])[S:11][C:12]=2[C:4]([C:1](=[O:3])[CH2:2][Br:22])=[CH:5][CH:6]=1)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 17977687Phenyltrimethylammonium bromide dibromideHCID 693219837-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

Product 1

HCID 859396374-(Benzyloxy)-7-(bromoacetyl)-1,3-benzothiazol-2(3H)-oneYield 93.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 7-acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one (68 mg) in dry THF (3 ml) under nitrogen, was added phenyltrimethylammonium tribromide (90 mg) and the mixture heated at 80° C. under nitrogen for 2 h. The mixture was diluted with water, extracted with ethyl acetate, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with stepped gradient of 10% to 100% ethyl acetate-cyclohexane mixtures, to give the title compound (49 mg).

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in vacuo
  5. customThe residue was purified on a 5 g silica SPE cartridge
  6. washeluting

Sources & evidence

ORD record
ord-400103016d584ac1b294435029fd05bf
Source dataset
uspto-grants-2008_07
Patent number
US07402598B2

Reaction notes

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