Ethyl benzoylacetate → Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

HRID 394778

反応式

HRID 394778 の反応式
[C:1]1([C:7](=O)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[NH2:34][C:35]([NH2:37])=[S:36]>C(#N)C>[NH2:37][C:35]1[S:36][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:34]=1

参加物

5

反応物 3

HCID 7170Ethyl benzoylacetateHCID 2723790ThioureaHCID 21918218Hydroxy tosyloxy iodobenzene

生成物 1

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate収率 75.9%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
65 °C

実験手順

To a solution of ethyl 3-phenyl-3-oxopropionate (5.0 g, 26.0 mmol) in 100 mL of acetonitrile was added hydroxy(tosyloxy)iodobenzene (11.2 g, 28.6 mmol). The resulting suspension was stirred at 65° C. for 1 h at which time the reaction was a homogeneous solution. Thiourea (2.2 g, 28.6 mmol) was added and stirring was continued at 65° C. for 2 h. The mixture was cooled and concentrated, and the residue was taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated. The residue was triturated with ethyl ether to afford 4.9 g (70%) of the title compound as a yellow solid. 1H NMR (CDCl3) d 7.65 (m, 2H), 7.39 (m, 3H), 5.98 (broad s, 2H), 4.18 (q, 2H), 1.22 (t, 3H).

後処理

  1. stirringstirring
  2. waitwas continued at 65° C. for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. washwashed with saturated aq Na2CO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was triturated with ethyl ether

出典と根拠

ORDレコード
ord-0f7ec75b59b14721884206e1f615b0c5
出典データセット
uspto-grants-2003_08
特許番号
US06602895B2

関連ノート

読み込み中…