Acetonitrile → Ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate

HRID 1186108노트

반응식

HRID 1186108 반응식
C(#N)C.[N+:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[CH:13]([NH:15][CH2:16][C:17]#[N:18])[CH3:14])([O-:6])=[O:5].C([O-])(O)=O.[Na+].Cl[C:25]([O:27][CH2:28][CH3:29])=[O:26]>CCOC(C)=O.C(Cl)Cl>[C:17]([CH2:16][N:15]([CH:13]([C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=1[N+:4]([O-:6])=[O:5])[CH3:14])[C:25](=[O:26])[O:27][CH2:28][CH3:29])#[N:18]

참가 물질

7

반응물 4

HCID 6342AcetonitrileHCID 10928Ethyl chloroformateHCID 516892Sodium BicarbonateHCID 866252282-(1-(2-Nitrophenyl)ethylamino)acetonitrile

생성물 1

HCID 86625229Ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate수율 4%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8857Ethyl Acetate용매

실험 절차

Preparation of ethyl cyanomethyl(1-(2-nitrophenylethyl)carbamate (19): To the acetonitrile solution containing 2-(1-(2-nitrophenyl)ethylamino)acetonitrile (18) from the previous step was added saturated NaHCO3 (5 mL) and ethyl chloroformate (1.83 g, 16.86 mmol). The reaction mixture was stirred vigorously at room temperature for 14 hours. The reaction was diluted with EtOAc (50 mL) and washed with brine (40 mL). The separated organic phase was dried over Na2SO4, filtered, and concentrated. Purification (Biotage 40 s, 3:1 CH2Cl2:hexanes, then 100% CH2Cl2) provided 37.1 mg (0.134 mmol, 4% yield) of ethyl cyanomethyl(1-(2-nitrophenyl)ethyl)carbamate (19) as a light yellow oil.

후처리

  1. washwashed with brine (40 mL)
  2. dry with materialThe separated organic phase was dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customPurification (Biotage 40 s, 3:1 CH2Cl2

출처 및 근거

ORD 기록
ord-adddfb23df0f4c1a882db0c1f4b68a7f
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08673898B2

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