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Bromine → 5-Isopropyl-2-nitro-4-thiocyanato-phenylamine

HRID 23484
Notes
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Reaction equation

HRID 23484 reaction equation
[CH:1]([C:4]1[CH:5]=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([NH2:10])[CH:9]=1)([CH3:3])[CH3:2].[S-:14][C:15]#[N:16].[Na+].[Br-].[Na+].BrBr>CO>[CH:1]([C:4]1[C:5]([S:14][C:15]#[N:16])=[CH:6][C:7]([N+:11]([O-:13])=[O:12])=[C:8]([NH2:10])[CH:9]=1)([CH3:3])[CH3:2]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 24408BromineHCID 253881Sodium BromideHCID 516871Sodium thiocyanateHCID 225728525-Isopropyl-2-nitroaniline

Product 1

HCID 225729135-Isopropyl-2-nitro-4-thiocyanato-phenylamine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent
On this pageParticipantsProcedureWorkupSources & evidenceReaction notes

Procedure

The title compound was prepared according to General Method 13 using 5-isopropyl-2-nitro-phenylamine (prepared in Example PP-1; 5.4 g, 30 mmol), sodium thiocyanate (14.6 g, 180 mmol), sodium bromide (3.7 g, 35.99 mmol), bromine (5.75 g, 36.0 mmol), and MeOH (100 mL). The crude reaction mixture was purified by flash silica gel chromatography (5%-50% EtOAc in hexanes as eluents). MS(APCI): 238 (M+H).

Workup

  1. customThe crude reaction mixture
  2. customwas purified by flash silica gel chromatography (5%-50% EtOAc in hexanes as eluents)

Sources & evidence

ORD record
ord-233cc62428524c4396e8779a88af5ae1
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852711B2

Reaction notes

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