Dimethylformamide → 7-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

HRID 749240ノート

反応式

HRID 749240 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]([OH:14])=[CH:6][CH:5]=1)(=[O:3])[CH3:2].CN(C=O)C.C(N(CC)C(C)C)(C)C.[CH2:29](Br)[C:30]1[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1>C1COCC1.O>[C:1]([C:4]1[C:12]2[S:11][C:10](=[O:13])[NH:9][C:8]=2[C:7]([O:14][CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)=[CH:6][CH:5]=1)(=[O:3])[CH3:2]

参加物

7

反応物 4

HCID 6228DimethylformamideHCID 7498Benzyl BromideHCID 81531DiisopropylethylamineHCID 450769877-Acetyl-4-hydroxybenzo[d]thiazol-2(3H)-one

生成物 1

HCID 693219837-Acetyl-4-(benzyloxy)-1,3-benzothiazol-2(3H)-one

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a solution of 7-acetyl-4-hydroxy-1,3-benzothiazol-2(3H)-one (153 mg), in dry THF (3 ml) and dry DMF (0.5 ml) under nitrogen, was added N,N-diisopropylethylamine (0.13 ml) and benzyl bromide (0.09 ml), and the mixture stirred for 72 h. Water (10 ml) was added and the mixture extracted with ethyl acetate. The organic phases were combined, washed with brine, dried (MgSO4), and evaporated in vacuo. The residue was purified on a 5 g silica SPE cartridge, eluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures, to give the title compound (68 mg). LCMS RT=3.14 min.

後処理

  1. extractionthe mixture extracted with ethyl acetate
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. customevaporated in vacuo
  5. customThe residue was purified on a 5 g silica SPE cartridge
  6. washeluting with a stepped gradient of 10% to 50% ethyl acetate-cyclohexane mixtures

出典と根拠

ORDレコード
ord-b853c45fcafa4252a8f6ce0233d3b0e2
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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