Aluminum(III) Chloride → HCID 57628288, compound

HRID 1692061Notes

Reaction equation

HRID 1692061 reaction equation
[Cl-].[Al+3].[Cl-].[Cl-].[NH2:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1/[C:11](=[CH:13]/[CH:14]([CH3:16])[CH3:15])/[CH3:12].NC1C=CSC=1/C(=C\C(C)C)/C>>[NH2:5][C:6]1[CH:10]=[CH:9][S:8][C:7]=1[C:11]([CH2:13][CH:14]([CH3:16])[CH3:15])=[CH2:12]

Participants

4

Reactant 3

HCID 6451240Aluminum(III) ChlorideHCID 44139031HCID 44139031, compoundHCID 57628287HCID 57628287, compound

Product 1

HCID 57628288HCID 57628288, compoundYield 12%

Procedure

Into a solution obtained by dissolving 3-aminothiophene (2.0 g, 20.6 mmol) in 4-methyl-2-pentanone (28.3 g), which was obtained by the method in Example 14 using methyl 3-aminothiophene-2-carboxylate as a starting material was added aluminum chloride (1.3 g, 24.5 mmol) at room temperature, and the resulting solution was stirred under nitrogen atmosphere at 60 degree centigrade for 5 hours. The reaction solution was cooled to room temperature, and then washed with a 10% aqueous sodium hydroxide solution, and separated. As a result of the analysis by the HPLC internal standard method of the obtained organic layer, 0.4 g was produced as a mixture of three compounds including 3-amino-2-{(E)-(4-methyl-2-penten-2-yl)}thiophene, 3-amino-2-{(Z)-(4-methyl-2-penten-2-yl)}thiophene and 3-amino-2-(4-methyl-1-penten-2-yl)thiophene (yield: 12%).

Workup

  1. washwashed with a 10% aqueous sodium hydroxide solution
  2. customseparated
  3. customAs a result of the analysis by the HPLC internal standard method of the obtained organic layer
  4. custom0.4 g was produced as a mixture of three compounds

Sources & evidence

ORD record
ord-eba32c8cd4524634bf74093dde8206f8
Source dataset
uspto-grants-2012_04
Patent number
US08153823B2

Reaction notes

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