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

HRID 749241ノート

反応式

HRID 749241 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
80 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-400103016d584ac1b294435029fd05bf
出典データセット
uspto-grants-2008_07
特許番号
US07402598B2

反応ノート

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