Water → (Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxyurea

HRID 2371478노트

반응식

HRID 2371478 반응식
[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][NH:23][OH:24].C[Si]([N:29]=[C:30]=[O:31])(C)C.O.C(OCC)(=O)C>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)/[C:7](=[CH:11]\[C:12]1[CH:17]=[CH:16][C:15]([S:18][CH3:19])=[CH:14][CH:13]=1)/[C:6]([CH3:20])=[C:5]2[CH2:21][CH2:22][N:23]([OH:24])[C:30]([NH2:29])=[O:31]

참가 물질

6

반응물 4

HCID 962WaterHCID 8857Ethyl AcetateHCID 70696Trimethylsilyl isocyanateHCID 86745522(Z)-3-(2-hydroxaminoethyl)-5-fluoro-2-methyl-1-(4-methylthiobenzylidene)indene

생성물 1

HCID 10221633(Z)-N-{2-[5-Fluoro-2-methyl-1-(4-methylthiobenzylidene)inden-3-yl]ethyl}-N-hydroxyurea

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a solution of the hydroxylamine intermediate from Step 4 (1.62 g, 4.7 mmol) in THF (15 mL) there was added 85% trimethylsilyl isocyanate (954 mg, 7.25 mmol). The mixture was stirred at room temperature for 30 minutes. Water (10 mL) was added and stirring was continued for a further 10 minutes. Ethyl acetate was then added, the organic layer was decanted, washed with brine, dried over MgSO4 and evaporated to dryness. The residue was triturated with ether and filtered to afford the pure title product as a yellow solid, mp: 149° C. dec.

후처리

  1. stirringstirring
  2. waitwas continued for a further 10 minutes
  3. customthe organic layer was decanted
  4. washwashed with brine
  5. dry with materialdried over MgSO4
  6. customevaporated to dryness
  7. customThe residue was triturated with ether
  8. filtrationfiltered

출처 및 근거

ORD 기록
ord-0af7910501f644da8b256e82dd95481e
출처 데이터셋
uspto-grants-1992_03
특허 번호
US05093356

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