Benzyl chloroformate → benzyl N-(3-cyano-2-methylphenyl)carbamate

HRID 2361268Notes

Reaction equation

HRID 2361268 reaction equation
[NH2:1][C:2]1[C:3]([CH3:10])=[C:4]([CH:7]=[CH:8][CH:9]=1)[C:5]#[N:6].[C:11](Cl)(=[O:20])[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>O1CCCC1>[C:5]([C:4]1[C:3]([CH3:10])=[C:2]([NH:1][C:11](=[O:20])[O:12][CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[CH:9]=[CH:8][CH:7]=1)#[N:6]

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 11430Potassium CarbonateHCID 2548423-Amino-2-methylbenzonitrile

Product 1

HCID 67994690benzyl N-(3-cyano-2-methylphenyl)carbamateYield 73.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 3-amino-2-methylbenzonitrile (4.32 g, 32.7 mmol), benzyl carbonochloridate (7.26 mL, 49.0 mmol), and potassium carbonate (6.78 g, 79.0 mmol) in tetrahydrofuran (280 mL) was stirred at room temperature for 3 days. The insoluble material was removed by filtration, and the filtrate was concentrated under vacuum. The residue was diluted with ethyl acetate (250 mL), washed with 1N HCl solution (60 mL), water (60 mL), and brine (60 mL). The organic solution was dried over anhydrous MgSO4, and the solution was concentrated under vacuum to dryness. The residue was stirred with hexane (100 mL) at room temperature for 1 hr. The insoluble product (6.41 g, 24.07 mmol, 73.6% yield) was collected as a white solid by suction filtration.

Workup

  1. customThe insoluble material was removed by filtration
  2. concentrationthe filtrate was concentrated under vacuum
  3. additionThe residue was diluted with ethyl acetate (250 mL)
  4. washwashed with 1N HCl solution (60 mL), water (60 mL), and brine (60 mL)
  5. dry with materialThe organic solution was dried over anhydrous MgSO4
  6. concentrationthe solution was concentrated under vacuum to dryness
  7. stirringThe residue was stirred with hexane (100 mL) at room temperature for 1 hr

Sources & evidence

ORD record
ord-f696a65392464c4195556d82a534cc64
Source dataset
uspto-grants-2014_04
Patent number
US08685969B2

Reaction notes

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