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

HRID 1186108Notes

Reaction equation

HRID 1186108 reaction equation
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]

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-adddfb23df0f4c1a882db0c1f4b68a7f
Source dataset
uspto-grants-2014_03
Patent number
US08673898B2

Reaction notes

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