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

HRID 1186108

反応式

HRID 1186108 の反応式
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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8857Ethyl Acetate溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-adddfb23df0f4c1a882db0c1f4b68a7f
出典データセット
uspto-grants-2014_03
特許番号
US08673898B2

関連ノート

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