Ethanol → HCID 178518070, 화합물

HRID 474296

반응식

HRID 474296 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]([NH:12][C:13]1C(Cl)=N[CH:16]=[N:17][C:18]=1Cl)=O.N[C:22]([NH2:24])=[S:23].CC[OH:27]>C(O)=O>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][C:10]1[S:23][C:22]2[N:24]=[CH:16][N:17]=[C:18]([OH:27])[C:13]=2[N:12]=1

참가 물질

5

반응물 3

HCID 702EthanolHCID 2723790ThioureaHCID 577424622-(2,6-Dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide

생성물 1

HCID 178518070HCID 178518070, 화합물

시약·촉매·용매 1

HCID 284Formic Acid용매

반응 조건

온도
90 °C

실험 절차

To a mixture of 2-(2,6-dichloro-phenyl)-N-(4,6-dichloro-pyrimidin-5-yl)-acetamide (77.0 g, 221 mmol), thiourea (16.8 g, 221 mmol), and EtOH (500 mL) was added formic acid (3 mL) at rt. The resulting mixture was heated to 90° C. After 12 h, the reaction mixture was cooled and concentrated. The resulting residue was collected by filtration and washed with H2O (100 mL) followed by hexanes (100 mL). The title compound as a dark brown solid was further dried by high vacuum for 12 h and used crude (68 g, 70% apparent purity by analytical HPLC). An analytically pure sample could be obtained by purified by preparative reverse-phase HPLC to afford the title compound as a colorless solid. MS (ESI): mass calcd. for C12H7Cl2N3OS, 310.9; m/z found, 312.0 [M+H]+. 1H NMR (CD3OD): 8.04 (s, 1H), 7.44-7.37 (m, 2H), 7.31-7.26 (m, 1H), 4.70 (s, 2H).

후처리

  1. temperaturethe reaction mixture was cooled
  2. concentrationconcentrated
  3. filtrationThe resulting residue was collected by filtration
  4. washwashed with H2O (100 mL)
  5. dry with materialThe title compound as a dark brown solid was further dried by high vacuum for 12 h
  6. customAn analytically pure sample could be obtained
  7. customby purified by preparative reverse-phase HPLC

출처 및 근거

ORD 기록
ord-76fe67d1e0a04e98a806f20939ee0395
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08637527B2

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