Aniline → Benzo(b)thiophen-3-amine, 2-nitro-N-phenyl-

HRID 2174146Notes

Reaction equation

HRID 2174146 reaction equation
Br[C:2]1[C:3]2[CH:13]=[CH:12][CH:11]=[CH:10][C:4]=2[S:5][C:6]=1[N+:7]([O-:9])=[O:8].[NH2:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.C(N(CC)CC)C>CN(C=O)C>[N+:7]([C:6]1[S:5][C:4]2[CH:10]=[CH:11][CH:12]=[CH:13][C:3]=2[C:2]=1[NH:14][C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)([O-:9])=[O:8]

Participants

5

Reactant 3

HCID 6115AnilineHCID 8471TriethylamineHCID 2970503-Bromo-2-nitro-benzo(b)thiophene

Product 1

HCID 197891Benzo(b)thiophen-3-amine, 2-nitro-N-phenyl-Yield 96%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture solution of 3-bromo-2-nitrobenzo[b]thiophene (14 g, 54 mmol), aniline (14 ml, 154 mmol) and triethylamine (11 ml, 79 mmol) in DMF (150 ml) was heated at 120° C. for 30 min before quenching with water. The solid was isolated by filtration, washed with water and recrystallized from DCM/hexane to yield 2-nitro-N-phenylbenzo[b]thiophen-3-amine (14 g, 96%) as a yellow solid.

Workup

  1. custombefore quenching with water
  2. customThe solid was isolated by filtration
  3. washwashed with water
  4. customrecrystallized from DCM/hexane

Sources & evidence

ORD record
ord-1c03dff9478f4373aa8ea9aafd36a0f8
Source dataset
uspto-grants-2015_06
Patent number
US09059412B2

Reaction notes

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