Sodium Chloride → HCID 178490609, 화합물

HRID 66637

반응식

HRID 66637 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12]Cl)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Mg:19].FCC#N.[C-]#N.[Na+].[Cl-:27].[NH4+].[Cl-].[Na+]>O1CCCC1.O>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([CH:14]=[CH:15][C:16]=1[O:17][CH3:18])[CH2:12][Mg:19][Cl:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

9

반응물 6

HCID 5234Sodium ChlorideHCID 8929Sodium CyanideHCID 10420Acetonitrile, fluoro-HCID 25517Ammonium ChlorideHCID 2802242-(Benzyloxy)-4-(chloromethyl)-1-methoxybenzeneHCID 5462224Magnesium

생성물 1

HCID 178490609HCID 178490609, 화합물

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-30 °C

실험 절차

Under an atmosphere of nitrogen, 3-benzyloxy-4-methoxybenzyl magnesium chloride is prepared from 3-benzyloxy-4-methoxybenzylchloride (C. Schopf and L. Winterhalder, Ann. 544, 62 (1940) (22.0 g, 84 mmol) and magnesium turnings (4.1 g) in tetrahydrofuran (THF) (100 ml) at room temperature (about 2 hours). After cooling to -30° C., a solution of fluoroacetonitrile (4.94 g) in THF (40 ml) is added dropwise, maintaining the temperature between -30° C. and -40° C. Stirring is continued at this temperature for another 30 minutes, then the mixture is poured into a solution of sodium cyanide (12.3 g) and ammonium chloride (17.9 g) in water (150 ml), previously cooled with ice. After stirring for 30 minutes, the mixture is saturated with sodium chloride whereupon the phases separate. After extracting the aqueous phase two more times with diethyl ether, the combined THF and ether phases are dried (Na2SO4) and evaporated to give the crude aminonitrile (25.9 g) as a brown oil. The oil is dissolved in ether and treated with HCl gas to prepare the hydrochloride as an oil. This oil is recrystallized twice from ethanol/ether to give 2-fluoromethyl-2-amino-3-(3'-benzyloxy-4'-methoxyphenyl)propionitrile as the hydrochloride as a slightly colored solid; NMR (CD3OC): 3.47 ppm (3H, s), 4.32 ppm (2H, d, JH--F =46 Hz), 4.73 ppm (2H, s), 6.60 ppm (3H, m), 6.97 ppm (5H, m).

후처리

  1. customat room temperature
  2. custom(about 2 hours)
  3. temperaturemaintaining the temperature between -30° C. and -40° C
  4. temperaturepreviously cooled with ice
  5. stirringAfter stirring for 30 minutes
  6. customseparate
  7. extractionAfter extracting the aqueous phase two more times with diethyl ether
  8. dry with materialthe combined THF and ether phases are dried (Na2SO4)
  9. customevaporated
  10. customto give the crude aminonitrile (25.9 g) as a brown oil

출처 및 근거

ORD 기록
ord-a3ef8b34366e4a66a317bdcc6edb8c68
출처 데이터셋
uspto-grants-1982_08
특허 번호
US04342780

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