Ammonia → HCID 178419392, compound

HRID 1489592Notes

Reaction equation

HRID 1489592 reaction equation
CS[C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][CH:9]=[N:10]2)=[C:5]2[NH:13][CH:14]=[N:15][C:4]=12.[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20].Cl.BrC1C=C(C=CC=1)N.N>>[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][CH:9]=[N:10]2)=[C:5]2[NH:13][CH:14]=[N:15][C:4]=12

Participants

5

Reactant 4

HCID 222AmmoniaHCID 115623-BromoanilineHCID 227368263-Bromoaniline--hydrogen chloride (1/1)HCID 178503063HCID 178503063, compound

Product 1

HCID 178419392HCID 178419392, compoundYield 77%

Procedure

A solution of 4-methylthioimidazo[4,5-f]quinazoline (0.43 g, 2 mmol), 3-bromoaniline (0.5 g, 3 mmol), and 3-bromoaniline hydrochloride (0.63 g, 3 mmol) is heated under reflux for 16 h. The precipitate of hydrochloride salt is converted directly to the free base with aqueous NH3, and recrystallized from EtOH to give 4-(3-bromoanilino)imidazo[4,5-f]quinazoline (0.52 g, 77%). 1H NMR (DMSO) δ11.53 (1H, brs), 8.79 (1H, s), 8.68 (1H, s), 8.53 (1H, dd, J=1.8, 1.9 Hz), 8.15 (1H, d, J=8.8 Hz), 7.81 (1H, brd, J=8.6 Hz), 7.71 (1H, d, J=8.9 Hz, 1H), 7.41 (1H, t, J=8.0 Hz), 7.32 (1H, brd, J=7.8 Hz).

Workup

  1. temperatureunder reflux for 16 h
  2. customrecrystallized from EtOH

Sources & evidence

ORD record
ord-832d4722294a4e918b58bc397255dd59
Source dataset
uspto-grants-1997_10
Patent number
US05679683

Reaction notes

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