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

HRID 394778

반응식

HRID 394778 반응식
[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

참가 물질

5

반응물 3

HCID 7170Ethyl benzoylacetateHCID 2723790ThioureaHCID 21918218Hydroxy tosyloxy iodobenzene

생성물 1

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

시약·촉매·용매 1

HCID 6342Acetonitrile용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-0f7ec75b59b14721884206e1f615b0c5
출처 데이터셋
uspto-grants-2003_08
특허 번호
US06602895B2

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