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

HRID 749240노트

반응식

HRID 749240 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-b853c45fcafa4252a8f6ce0233d3b0e2
출처 데이터셋
uspto-grants-2008_07
특허 번호
US07402598B2

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