Pyridine → Phenyl 4-carbamoylphenylcarbamate

HRID 404491Notes

Reaction equation

HRID 404491 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([NH2:8])=[O:7])=[CH:4][CH:3]=1.N1C=CC=CC=1.Cl[C:18]([O:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)=[O:19].CCCCC>C(Cl)Cl.C(OCC)C>[C:6]([C:5]1[CH:9]=[CH:10][C:2]([NH:1][C:18](=[O:19])[O:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)=[CH:3][CH:4]=1)(=[O:7])[NH2:8]

Participants

7

Reactant 4

HCID 1049PyridineHCID 8003PentaneHCID 15891Phenyl chloroformateHCID 760794-Aminobenzamide

Product 1

HCID 60631229Phenyl 4-carbamoylphenylcarbamateYield 77%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
-10 °C

Procedure

To a solution of 4-aminobenzamide (5.0 g, 36.7 mmol) and pyridine (2.9 g, 36.7 mmol)) in dry CH2Cl2 (100 mL) at −10° C., phenyl chloroformate (6.9 g, 44.1 mmol) was added dropwise, stirred at −10° C. for 30 min and then at room temperature for 30 minutes The reaction mixture was diluted with CH2Cl2 (100 mL) and washed with water (2×70 mL). The organic layer was dried over anhydrous Na2SO4 and concentrated to get the crude product. The crude product was dissolved in diethyl ether (15 mL) and sonicated for 10 minutes and then pentane (30 mL) was added, the resulting solid was filtered and washed with pentane to give phenyl 4-carbamoylphenylcarbamate (7.2 g, 77% yield).

Workup

  1. washwashed with water (2×70 mL)
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated
  4. customto get the crude product
  5. customsonicated for 10 minutes
  6. filtrationthe resulting solid was filtered
  7. washwashed with pentane

Sources & evidence

ORD record
ord-d565ddcdcdcc434994b9712438cfa488
Source dataset
uspto-grants-2014_06
Patent number
US08748421B2

Reaction notes

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