Sodium hydride → HCID 178448128, 화합물

HRID 1419803노트

반응식

HRID 1419803 반응식
[H-].[Na+].[C:3]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([OH:12])[CH2:8][CH2:7]1)([CH3:5])=[CH2:4].Cl[C:14]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[N:17]=[CH:16][N:15]=1.[Cl-].[NH4+]>C1COCC1.C(O)(C)C>[C:3]([C@@H:6]1[CH2:11][CH2:10][C@H:9]([O:12][C:14]2[C:23]3[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=3)[N:17]=[CH:16][N:15]=2)[CH2:8][CH2:7]1)([CH3:5])=[CH2:4]

참가 물질

7

반응물 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 788644-ChloroquinazolineHCID 178448129HCID 178448129, 화합물

생성물 1

HCID 178448128HCID 178448128, 화합물

시약·촉매·용매 2

HCID 3776Isopropanol용매HCID 8028Tetrahydrofuran용매2회

실험 절차

0.42 g (17.5 mmol) of NaH (80% pure) was added in portions to a solution of 1.8 g (12.8 mmol) of cis-4isopropenylcyclohexanol in 20 ml of absolute THF. The mixture was then heated at reflux for 3 hours, and a solution of 1.9 g (11.6 mmol) of 4-chloroquinazoline in 10 ml of THF was added dropwise. The reaction mixture was subsequently heated at reflux for 5 hours. After cooling to room temperature, 10 ml of isopropanol were added, the mixture was subsequently stirred for 15 minutes, and the reaction solution was poured into saturated ammonium chloride solution. Extraction was carried out with ether, the combined organic phases were dried over MgSO4 and the solvent was concentrated by evaporation in vacuo. The residue (2.7 g) was purified by flash chromatography over silica gel with petroleum ether/ethyl acetate 3:1. After concentration, 1.8 g (57.6% of theory) were obtained of a colorless oil.

후처리

  1. temperatureThe mixture was then heated
  2. temperatureat reflux for 3 hours
  3. temperatureThe reaction mixture was subsequently heated
  4. temperatureat reflux for 5 hours
  5. extractionExtraction
  6. dry with materialthe combined organic phases were dried over MgSO4
  7. concentrationthe solvent was concentrated by evaporation in vacuo
  8. customThe residue (2.7 g) was purified by flash chromatography over silica gel with petroleum ether/ethyl acetate 3:1
  9. concentrationAfter concentration
  10. custom1.8 g (57.6% of theory) were obtained of a colorless oil

출처 및 근거

ORD 기록
ord-3e03fbdb49ad43859eaaee978c67eb5d
출처 데이터셋
uspto-grants-1999_03
특허 번호
US05889012

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