3-Bromoaniline → HCID 18184414, compound

HRID 1358274Notes

Reaction equation

HRID 1358274 reaction equation
CS[C:3]1[C:12]2[N:13]=[CH:14][NH:15][C:11]=2[C:10]2[N:9]=[CH:8][N:7]=[CH:6][C:5]=2[CH:4]=1.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].[ClH:24].BrC1C=C(C=CC=1)N>CN1CCCC1=O>[ClH:24].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][C:3]1[C:12]2[N:13]=[CH:14][NH:15][C:11]=2[C:10]2[N:9]=[CH:8][N:7]=[CH:6][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 227368263-Bromoaniline--hydrogen chloride (1/1)HCID 178503062HCID 178503062, compound

Product 1

HCID 18184414HCID 18184414, compoundYield 61.1%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 4-methylthioimidazo[4,5-h]quinazoline (0.216 g, 1 mmol), 3-bromoaniline (0.25 g, 1.5 mmol), and 3-bromoaniline hydrochloride (0.31 g, 1.5 mmol) in N-methylpyrrolidone (50 mL) is heated 120° C. for 2 h. The solvent is removed under vacuum and the residue is triturated with EtOH to give a solid which is recrystallized from MeOH to give 4-(3-bromoanilino)imidazo[4,5-h]quinazoline hydrochloride (0.23 g, 61%). 1H NMR (DMSO) δ11.11 (1H, brs), 8.93 (2H, s), 8.66 (1H, d, J=9.0 Hz), 8.11 (1H, brs), 8.07 (1H, d, J=9.0 Hz), 7.83 (1H, brd, J=6.8 Hz), 7.50-7.40 (2H,m).

Workup

  1. customThe solvent is removed under vacuum
  2. customthe residue is triturated with EtOH
  3. customto give a solid which
  4. customis recrystallized from MeOH

Sources & evidence

ORD record
ord-c095c15f2d3c4bcc811008a06fdc6006
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

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