Benzoyl isocyanate → N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide

HRID 471626Notes

Reaction equation

HRID 471626 reaction equation
[NH2:1][C:2]1[CH:9]=[CH:8][CH:7]=[C:6]([NH:10][CH3:11])[C:3]=1[C:4]#[N:5].[C:12]([N:20]=[C:21]=[O:22])(=[O:19])[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>O1CCOCC1>[C:4]([C:3]1[C:6]([NH:10][CH3:11])=[CH:7][CH:8]=[CH:9][C:2]=1[NH:1][C:21]([NH:20][C:12](=[O:19])[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1)=[O:22])#[N:5]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 127157172-Amino-6-(methylamino)benzonitrile

Product 1

HCID 67401506N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamideYield 20%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 2-amino-6-(methylamino)benzonitrile (example 156b) (0.14 g, 0.97 mmol) in 1,4-dioxane (3 mL) was added benzoyl isocyanate (0.17 g, 1.17 mmol). The reaction mixture was stirred at room temperature under nitrogen overnight. The obtained precipitate was filtered and dried under vacuum to give N-(2-cyano-3-(methylamino)phenylcarbamoyl)benzamide (57 mg, 20%). 1H NMR (400 MHz, DMSO-d6) δ 2.75 (d, J=4.4 Hz, 3H), 6.26 (d, J=4.8 Hz, NH), 6.43 (d, J=9.6 Hz, 1H), 7.40-7.43 (m, 2H), 7.51-7.55 (m, 2H), 7.63-7.65 (m, 1H), 8.01 (d, J=8.4 Hz, 2H), 11.23 (s, NH), 11.30 (s, NH). MS 295 (MH+).

Workup

  1. filtrationThe obtained precipitate was filtered
  2. customdried under vacuum

Sources & evidence

ORD record
ord-0550d2542d9746a79cce10b578bc590c
Source dataset
uspto-grants-2014_01
Patent number
US08633186B2

Reaction notes

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