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Diethylamine → 4-(Diethylamino)benzonitrile

HRID 449
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HRID 449 반응식
CCNCC.N#Cc1ccc(Br)cc1>CC#N.CC(=O)O.CC(=O)O.CC(C)c1cc(C(C)C)c(-c2ccccc2P(C2CCCCC2)C2CCCCC2)c(C(C)C)c1.O=C([O-])[O-].[K+].[K+].[Pd]>CCN(CC)c1ccc(C#N)cc1
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참가 물질

7

반응물 2

HCID 8021DiethylamineHCID 12162Benzonitrile, 4-bromo-

생성물 1

HCID 761344-(Diethylamino)benzonitrile수율 39.17%

시약·촉매·용매 4

HCID 11430Potassium Carbonate시약HCID 4144353Palladium (II) acetate촉매HCID 11155794
2-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenyl
촉매
HCID 6342Acetonitrile용매

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온도
160 °C

실험 절차

4-Bromobenzonitrile (2.000 g, 10.99 mmol), diethylamine (3.41 mL, 32.96 mmol) and POTASSIUM CARBONATE (4.56 g, 32.96 mmol) were mixed in dry acetonitrile (10 mL) under argon in a microwave vial. The vial was sealed and heated with microvawes for 60 minutes at 160°C. Added diethylamine (3.41 mL, 32.96 mmol) and heated at 160°C for 3 hours. Added Palladium(II) acetate (0.123 g, 0.55 mmol) and 2-(Dicyclohexylphosphino)-2',4',6'-tri-i- propyl-1,1'-biphenyl (0.524 g, 1.10 mmol), purged with argon for 5 minutes and heated in an oil bath at 100°C for 24 hours. The reaction was cooled to rt and partitioned between EtOAc (100 mL) and saturated aqueous NaHCO3 (40 mL). The layers were separated and the aqueous phase extracted with EtOAc (100 mL). The organics were combined, dried (Na2SO4), filtered and concentrated. Purification by flash chromatography on silica gel gave 4-(diethylamino)benzonitrile (0.750 g, 39.2 %)

출처 및 근거

ORD 기록
ord-45a7a9da12934ab5ab153542a819eb23
출처 데이터셋
750 AstraZeneca ELN dataset
원본 링크
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