Benzoyl isocyanate → N-(2-cyano-5-hydroxyphenylcarbamoyl)benzamide

HRID 44389Notes

Reaction equation

HRID 44389 reaction equation
[NH2:1][C:2]1[CH:9]=[C:8]([OH:10])[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([N:19]=[C:20]=[O:21])(=[O:18])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1>CC(C)=O>[C:4]([C:3]1[CH:6]=[CH:7][C:8]([OH:10])=[CH:9][C:2]=1[NH:1][C:20]([NH:19][C:11](=[O:18])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1)=[O:21])#[N:5]

Participants

4

Reactant 2

HCID 78210Benzoyl isocyanateHCID 124686832-Amino-4-hydroxybenzonitrile

Product 1

HCID 57456929N-(2-cyano-5-hydroxyphenylcarbamoyl)benzamide

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Prepared as in Example 53a, but refluxed in acetone instead of 1,4-dioxane, from 2-amino-4-hydroxybenzonitrile and benzoyl isocyanate as a yellow solid (399 mg, 94%). MS 281 (MH+).

Workup

  1. customPrepared as in Example 53a

Sources & evidence

ORD record
ord-be683f1801f342f19138a097279c7dc1
Source dataset
uspto-grants-2013_09
Patent number
US08541421B2

Reaction notes

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