3-Bromoaniline → N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamide

HRID 1068971Notes

Reaction equation

HRID 1068971 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH:6]=[CH:7][C:8]=1[N:9]=[CH:10][N:11](C)C)#[N:2].[Br:20][C:21]1[CH:22]=[C:23]([CH:25]=[CH:26][CH:27]=1)N>C(O)(=O)C>[Br:20][C:21]1[CH:27]=[C:26]([NH:2][C:1]2[C:3]3[C:8](=[CH:7][CH:6]=[C:5]([NH:14][C:15](=[O:19])[C:16]#[C:17][CH3:18])[CH:4]=3)[N:9]=[CH:10][N:11]=2)[CH:25]=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 115623-BromoanilineHCID 18350692N-[3-Cyano-4-[[(dimethylamino)methylene]amino]phenyl]-2-butynamide

Product 1

HCID 2776N-(4-((3-bromophenyl)amino)-6-quinazolinyl)-2-butynamide

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of 3.0 g (11.8 mmol) of N-[3-cyano-4-[[(dimethylamino)methylene]amino]phenyl]-2-butynamide and 2.23 g (12.98 mmol) of 3-bromo aniline in 18 mL of acetic acid was refluxed gently with stirring under nitrogen for 1 hr 15 min. The mixture was cooled in an ice bath and a solid mass formed. The solid was collected by filtration and washed with ether-acetonitrile 1:1 to give a yellow solid which was recrystallized from ethanol giving 2.51 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide: mass spectrum (m/e): 381, 383.

Workup

  1. temperatureThe mixture was cooled in an ice bath
  2. customa solid mass formed
  3. filtrationThe solid was collected by filtration
  4. washwashed with ether-acetonitrile 1:1
  5. customto give a yellow solid which
  6. customwas recrystallized from ethanol giving 2.51 g of N-[4-[(3-bromophenyl)amino]-6-quinazolinyl]-2-butynamide

Sources & evidence

ORD record
ord-c6e1d44adabb4d3cb909984cf455c76f
Source dataset
uspto-grants-2001_06
Patent number
US06251912B1

Reaction notes

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