Sodium Cyanide → 2-Amino-2-(fluoromethyl)-5-methoxypentanenitrile

HRID 1607753

반응식

HRID 1607753 반응식
[CH3:1][O:2][CH2:3][CH2:4][CH2:5]Cl.[Mg:7].[F:8][CH2:9][C:10]#[N:11].[C-:12]#[N:13].[Na+].[Cl-:15].[NH4+]>C1COCC1.O>[CH3:1][O:2][CH2:3][CH2:4][CH2:5][Mg:7][Cl:15].[F:8][CH2:9][C:10]([NH2:11])([CH2:5][CH2:4][CH2:3][O:2][CH3:1])[C:12]#[N:13]

참가 물질

9

반응물 5

HCID 8929Sodium CyanideHCID 10420Acetonitrile, fluoro-HCID 25517Ammonium ChlorideHCID 1189271-Chloro-3-methoxypropaneHCID 5462224Magnesium

생성물 2

HCID 199663342-Amino-2-(fluoromethyl)-5-methoxypentanenitrile수율 99.9%HCID 178495109HCID 178495109, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-30 °C

실험 절차

Under an atmosphere of nitrogen, 3-methoxypropyl magnesium chloride is prepared from 3-methoxy-1-chloropropane (5.43 g, 50 mmol), prepared according to Haworth and Perking, Chem. Zentralblatt, II, 1271 (1912) and magnesium turnings (1.22 g, 50 mmol) in dry THF (50 ml). The mixture is heated under reflux for 3 hours, then cooled to -30° C. and a solution of fluoroacetonitrile (2.95 g, 50 mmol) in THF (30 mol) is added during 20 minutes. After keeping the mixture at -30° C. for 1/2 hour more, a solution of sodium cyanide (4.9 g, 100 mmol) and ammonium chloride (8.09 g, 150 mmol) in water (100 ml), previously cooled to 0° C., is added and the mixture is stirred for 3/4 hour at room temperature. After saturating with sodium chloride, the THF layer is separated and the aqueous phase is extracted twice with ether. After drying (Na2SO 4), the combined organic extracts are evaporated to give 2-fluoromethyl-2-amino-5-methoxypentanenitrile (4.0 g) as a brown oil.

후처리

  1. customprepared
  2. temperatureThe mixture is heated
  3. temperatureunder reflux for 3 hours
  4. customat -30° C.
  5. customfor 1/2 hour
  6. additionis added
  7. concentrationAfter saturating with sodium chloride
  8. customthe THF layer is separated
  9. extractionthe aqueous phase is extracted twice with ether
  10. dry with materialAfter drying (Na2SO 4)
  11. customthe combined organic extracts are evaporated

출처 및 근거

ORD 기록
ord-90131712d2604b749ec11003cd0f12e7
출처 데이터셋
uspto-grants-1989_09
특허 번호
US04866206

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