Hydrochloric Acid → HCID 86722772, 화합물

HRID 2203392

반응식

HRID 2203392 반응식
[F:1][C:2]([F:14])([F:13])[C:3]1[CH:4]=[C:5]([NH:9][C:10]([NH2:12])=[S:11])[CH:6]=[CH:7][CH:8]=1.[Br:15][C:16]1[CH:23]=[C:22]([C:24]#[N:25])[CH:21]=[CH:20][C:17]=1[CH:18]=O.[C:26]([O:32][CH3:33])(=[O:31])[CH2:27][C:28]([CH3:30])=O.C[Si](OP([O-])([O-])=O)(C)C.Cl>C1COCC1>[CH3:33][O:32][C:26]([C:27]1[CH:18]([C:17]2[CH:20]=[CH:21][C:22]([C:24]#[N:25])=[CH:23][C:16]=2[Br:15])[NH:12][C:10](=[S:11])[N:9]([C:5]2[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:1])([F:13])[F:14])[CH:4]=2)[C:28]=1[CH3:30])=[O:31]

참가 물질

7

반응물 5

HCID 313Hydrochloric AcidHCID 7757Methyl acetoacetateHCID 7358443-(Trifluoromethyl)phenylthioureaHCID 18172808TrimethylsilylphosphateHCID 205105183-Bromo-4-formylbenzonitrile

생성물 1

HCID 86722772HCID 86722772, 화합물수율 50%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
75 °C

실험 절차

3-Trifluoromethylphenylthiourea (12.8 g, 87 mmol), 2-bromo-4-cyanobenzaldehyde (18.3 g, 87 mmol), and methyl acetoacetate (10.4 mL, 96 mmol) were dissolved in THF (300 mL) under an atmosphere of N2 and then trimethylsilylphosphate (18 g) in THF (50 mL) was added, and the mixture heated at 75° C. After 17 hours the reaction mixture was allowed to cool, poured onto 0.5 M HCl (600 mL) and stirred for 30 minutes. The mixture was extracted into EtOAc. The organic phase was washed with water, then brine and dried (Na2SO4) before being concentrated in vacuo. The resulting solid was triturated with Et2O (50 mL), filtered and the solid collected to yield the title compound as a white solid (22.2 g).

후처리

  1. temperatureto cool
  2. extractionThe mixture was extracted into EtOAc
  3. washThe organic phase was washed with water
  4. dry with materialbrine and dried (Na2SO4)
  5. concentrationbefore being concentrated in vacuo
  6. customThe resulting solid was triturated with Et2O (50 mL)
  7. filtrationfiltered
  8. customthe solid collected

출처 및 근거

ORD 기록
ord-af3de181f6d14fd1a0a3cbdb6e80e403
출처 데이터셋
uspto-grants-2016_06
특허 번호
US09365577B2

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