HCID 44139031, compound → HCID 57628288, compound

HRID 1692065Notes

Reaction equation

HRID 1692065 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1/[C:7](=[CH:9]/[CH:10]([CH3:12])[CH3:11])/[CH3:8].NC1C=CSC=1/C(=C\C(C)C)/C>>[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([CH2:9][CH:10]([CH3:12])[CH3:11])=[CH2:8]

Participants

3

Reactant 2

HCID 44139031HCID 44139031, compoundHCID 57628287HCID 57628287, compound

Product 1

HCID 57628288HCID 57628288, compoundYield 76%

Procedure

95% Sulfuric acid (0.4 g, 3.9 mol) was added to a 0.5% 4-methyl-2-pentanone solution (30.0 g, 1.5 mmol) of 3-aminothiophene obtained by diluting a 4-methyl-2-pentanone solution of 3-aminothiophene, which was obtained in the same manner as in Example 14 using methyl-3-aminothiophene-2-carboxylate as a starting material at room temperature, and the resulting solution was stirred under nitrogen atmosphere at 60 degree centigrade for 6 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, 0.2 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: 76%).

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. custom0.2 g was produced as a mixture of three compounds

Sources & evidence

ORD record
ord-654df8895745402d810d4366aa45b354
Source dataset
uspto-grants-2012_04
Patent number
US08153823B2

Reaction notes

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