3-Bromoaniline → HCID 70023820, compound

HRID 1358267Notes

Reaction equation

HRID 1358267 reaction equation
CS[CH:3]1[C:12]2[N:11]=[CH:10][N:9]=[CH:8][C:7]=2[CH:6]=[C:5]2[N:13]=[N:14][N:15]=[C:4]12.[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>C(O)(C)C>[ClH:24].[Br:16][C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH:20][CH:3]1[C:12]2[N:11]=[CH:10][N:9]=[CH:8][C:7]=2[CH:6]=[C:5]2[N:13]=[N:14][N:15]=[C:4]12

Participants

5

Reactant 3

HCID 115623-BromoanilineHCID 227368263-Bromoaniline--hydrogen chloride (1/1)HCID 70024042HCID 70024042, compound

Product 1

HCID 70023820HCID 70023820, compoundYield 63.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A mixture of 4-methylthiotriazolo[4,5-g]quinazoline (0.30 g, 1.38 mmol), 3-bromoaniline (2.1 mmol) and 3-bromoaniline hydrochloride (2.1 mmol) in isopropanol (400 mL) is heated under reflux for 6 h, and the solution is concentrated to give 4-(3-bromoanilino)-triazolo[4,5-g]quinazoline hydrochloride (0.33 g, 63%). 1H NMR (DMSO) δ12.01 (1H, brs), 9.86 (1H, s), 9.02 (1H, s), 8.63 (1H, s), 8.39 (1H, s), 8.13 (1H, dd, J=1.9, 1.5 Hz), 7.85 (1H, ddd, J=7.7, 1.9, 1.5 Hz), 7.56 (1H, ddd, J=8.0, 1.7, 1.5 Hz), 7.41 (1H t, J=7.8 Hz).

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 6 h
  3. concentrationthe solution is concentrated

Sources & evidence

ORD record
ord-137b62d43d0d428f9464d13d87c29eb4
Source dataset
uspto-grants-2003_07
Patent number
US06596726B1

Reaction notes

Loading…