Thiourea → 2-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole

HRID 1062677노트

반응식

HRID 1062677 반응식
Br[CH:2]([C:8]([C:10]1[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=1)=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C>[NH2:21][C:19]1[S:20][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]#[N:17])[CH:11]=2)[N:18]=1

참가 물질

4

반응물 2

HCID 2723790ThioureaHCID 22282470Ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate

생성물 1

HCID 222824852-Amino-4-(3-cyanophenyl)-5-carboethoxythiazole수율 84%

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
80 °C

실험 절차

To a solution of ethyl 2-bromo-3-(3-cyanophenyl)-3-oxopropionate (2.0 g, 6.75 mmol) in 100 mL of absolute ethanol was added thiourea (0.51 g, 6.75 mmol). The resulting mixture was stirred at 80° C. for 3 h. The reaction was allowed to cool and the solvent was evaporated in vacuo. The residue was taken up in ethyl acetate, washed with saturated aq NaHCO3 and brine, dried (MgSO4) and concentrated in vacuo to yield a solid. Trituration with hexanes/ethyl ether left the title compound as an off-white solid (1.55 g, 65%). 1H NMR (DMSO-d6) δ: 8.03 (s, 1H); 7.93 (s, 2H) ; 7.91 (d, 1H); 7.82 (d, 1H); 7.58 (t, 1H); 4.05 (q, 2H); 1.10 (t, 3H).

후처리

  1. temperatureto cool
  2. customthe solvent was evaporated in vacuo
  3. washwashed with saturated aq NaHCO3 and brine
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated in vacuo
  6. customto yield a solid

출처 및 근거

ORD 기록
ord-b93404e3693540fba539d7881408544d
출처 데이터셋
uspto-grants-2005_11
특허 번호
US06962935B2

반응 노트

불러오는 중…