Benzyl chloroformate → Benzyl Cyanomethylcarbamate

HRID 2167788Notes

Reaction equation

HRID 2167788 reaction equation
C([O-])(O)=O.[Na+].S(O)(O)(=O)=O.[NH2:11][CH2:12][C:13]#[N:14].[CH2:15]([O:22][C:23](Cl)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>O.O1CCOCC1.C(Cl)Cl>[CH2:15]([O:22][C:23](=[O:24])[NH:14][CH2:13][C:12]#[N:11])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

7

Reactant 3

HCID 10387Benzyl chloroformateHCID 196971Aminoacetonitrile sulfate (1:1)HCID 516892Sodium Bicarbonate

Product 1

HCID 244143Benzyl CyanomethylcarbamateYield 56.8%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

NaHCO3 (1.09 g, 12.97 mmol) in water (5 mL) was added to a stirred solution of 2-aminoacetonitrile sulfate (1.0 g, 6.48 mmol) in 1,4-Dioxane (10 mL) at 0-5° C. followed by addition of Benzylchloroformate (1.3 g, 1.11 mL, 7.78 mmol) and stirring was continued at 20-35° C. for 15 h. Reaction mixture was diluted with DCM and washed it with water, dried over anhydrous sodium sulphate and concentrated under reduced pressure to afford the crude, which was purified by Column chromatography (using Silica gel 60-120 and 10% MeOH in DCM as eluent) to afford 700 mg of the title compound.

Workup

  1. customReaction mixture
  2. washwashed it with water
  3. dry with materialdried over anhydrous sodium sulphate
  4. concentrationconcentrated under reduced pressure
  5. customto afford the crude, which
  6. customwas purified by Column chromatography (using Silica gel 60-120 and 10% MeOH in DCM as eluent)

Sources & evidence

ORD record
ord-e21f0e07b1a14337bacb4f5731e16dc8
Source dataset
uspto-grants-2015_06
Patent number
US09045479B2

Reaction notes

Loading…