Benzoyl isocyanate → Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate

HRID 471526ノート

反応式

HRID 471526 の反応式
[NH2:1][C:2]1[S:6][C:5]([C:7]([O:9][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:8])=[C:4]([CH3:14])[C:3]=1[C:15]#[N:16].[C:17]([N:25]=[C:26]=[O:27])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>O1CCOCC1.CCOC(C)=O>[C:17]([NH:25][C:26](=[O:27])[NH:1][C:2]1[S:6][C:5]([C:7]([O:9][C:10]([CH3:12])([CH3:11])[CH3:13])=[O:8])=[C:4]([CH3:14])[C:3]=1[C:15]#[N:16])(=[O:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

参加物

5

反応物 2

HCID 78210Benzoyl isocyanateHCID 18445366Tert-butyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate

生成物 1

HCID 57456933Tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate収率 84.2%

試薬・触媒・溶媒 2

HCID 8857Ethyl Acetate溶媒HCID 312751,4-Dioxane溶媒

実験手順

To a solution of tert-butyl 5-amino-4-cyano-3-methylthiophene-2-carboxylate (example 64b) (16 g, 67.14 mmol) in dioxane (200 mL), was added benzoyl isocyanate (10 g, 67.14 mmol). The reaction mixture was stirred at rt overnight, and upon completion was diluted with EtOAc, washed with NaHCO3, water, brine, dried over MgSO4, filtered and concentrated to yield tert-butyl 5-(3-benzoylureido)-4-cyano-3-methylthiophene-2-carboxylate (21.78 g, 84%) as a brown solid. 1H NMR (400 MHz, DMSO-d6) δ 1.54 (s, 9H), 3.58 (s, 3H), 7.58 (t, J=7.5 Hz, 2H), 7.71 (t, J=7.5 Hz, 1H), 7.88 (d, J=7.5 Hz, 1H), 8.05 (d, J=7.5 Hz, 2H), 12.25 (br s, 1H).

後処理

  1. washwashed with NaHCO3, water, brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-7a5ce443da794bf2b41de6d64b565e85
出典データセット
uspto-grants-2014_01
特許番号
US08633186B2

反応ノート

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