Benzoyl isocyanate → N-(2-cyano-3-(2-methylprop-1-enyl)phenylcarbamoyl)benzamide

HRID 711758Notes

Reaction equation

HRID 711758 reaction equation
[C:1]([N:9]=[C:10]=[O:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C:13]1[CH:20]=[CH:19][CH:18]=[C:17]([CH:21]=[C:22]([CH3:24])[CH3:23])[C:14]=1[C:15]#[N:16]>O1CCOCC1>[C:15]([C:14]1[C:17]([CH:21]=[C:22]([CH3:23])[CH3:24])=[CH:18][CH:19]=[CH:20][C:13]=1[NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[O:11])#[N:16]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 673997672-Amino-6-(2-methylprop-1-enyl)benzonitrile

Product 1

HCID 67398450N-(2-cyano-3-(2-methylprop-1-enyl)phenylcarbamoyl)benzamideYield 89%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Benzoyl isocyanate (88.1 mg, 0.60 mmol) was added to a solution of 2-amino-6-(2-methylprop-1-enyl)benzonitrile (Example 129b) (75.2 mg, 0.44 mmol) in anhydrous 1,4-dioxane under nitrogen, and was stirred at room temperature for 12 h. The mixture was concentrated under vacuum, and purified by chromatography on silica gel eluting with solvent gradient 0% to 15% MeOH in CH2Cl2, to give 125.0 mg (86%) of N-(2-cyano-3-(2-methylprop-1-enyl)phenylcarbamoyl)benzamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.80 (d, J=1.2 Hz, 3H), 1.95 (d, J=1.2 Hz, 3H), 6.40 (s, 1H), 7.19 (m, 1H), 7.55 (m, 2H), 7.67 (m, 2H), 8.03 (m, 2H), 8.13 (m, 1H), 11.33 (s, 1H), 11.48 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated under vacuum
  2. custompurified by chromatography on silica gel eluting with solvent gradient 0% to 15% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-f3f8767c1b0e44cebd602b288c7fa77c
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

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