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

HRID 2371478ノート

反応式

HRID 2371478 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0af7910501f644da8b256e82dd95481e
出典データセット
uspto-grants-1992_03
特許番号
US05093356

反応ノート

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