2-Thiophenecarbonitrile → HCID 178512067, compound

HRID 2242889Notes

Reaction equation

HRID 2242889 reaction equation
[Br:1][C:2]1[C:3]([NH2:9])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1.[S:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]#[N:16].[Al+3].[Cl-].[Cl-].[Cl-]>ClC(Cl)C.O>[Br:1][C:2]1[C:3]([NH:9][C:15]([C:11]2[S:10][CH:14]=[CH:13][CH:12]=2)=[NH:16])=[N:4][CH:5]=[C:6]([Br:8])[N:7]=1

Participants

6

Reactant 3

HCID 660872-ThiophenecarbonitrileHCID 6200042-Amino-3,5-dibromopyrazineHCID 6451240Aluminum(III) Chloride

Product 1

HCID 178512067HCID 178512067, compoundYield 68.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 63651,1-DichloroethaneSolvent

Procedure

A stirred solution of 3,5-dibromo-pyrazin-2-ylamine (500 mg, 1.98 mmol), thiophene-2-carbonitrile (260 uL, 2.04 mmol) and AlCl3 (232 mg, 1.74 mmol) in dichloroethane (5 ml) was heated at 115° C. overnight. The mixture was allowed to cool to room temperature and diluted with water (5 mL). After 30 minutes, the resulting precipitate was collected and purified by column chromatography (SiO2, THF) to afford 488 mg (68%) of N-(3,5-dibromo-pyrazin-2-yl)-thiophene-2-carboxamidine as a yellow solid. 1H NMR (300 MHz, DMSO-d6) δ 7.22 (t, J=3.9 Hz, 1H), 7.83 (dd, J=4.8 Hz, 1H), 7.99 (d, J=4.1 Hz, 1H), 8.49 (s, 1H), 8.88 (br. s, 1H).

Workup

  1. customthe resulting precipitate was collected
  2. custompurified by column chromatography (SiO2, THF)

Sources & evidence

ORD record
ord-133bc8e75347492d8afd2e1895ba9646
Source dataset
uspto-grants-2010_03
Patent number
US07674791B2

Reaction notes

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