Hydrochloric Acid → HCID 57628288, compound

HRID 1692062Notes

Reaction equation

HRID 1692062 reaction equation
Cl.[NH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1/[C:8](=[CH:10]/[CH:11]([CH3:13])[CH3:12])/[CH3:9].NC1C=CSC=1/C(=C\C(C)C)/C>>[NH2:2][C:3]1[CH:7]=[CH:6][S:5][C:4]=1[C:8]([CH2:10][CH:11]([CH3:13])[CH3:12])=[CH2:9]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 44139031HCID 44139031, compoundHCID 57628287HCID 57628287, compound

Product 1

HCID 57628288HCID 57628288, compoundYield 14%

Procedure

Into a solution obtained by dissolving 3-aminothiophene (1.8 g, 18.1 mmol) in 4-methyl-2-pentanone (30.1 g), which was obtained in the same manner as in Example 14 using methyl 3-aminothiophene-2-carboxylate as a starting material was added concentrated hydrochloric acid (9.3 g, 90.5 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, 0.5 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: 14%).

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. custom0.5 g was produced as a mixture of three compounds

Sources & evidence

ORD record
ord-81b13e0e978d447eab009fc8b8fe63f8
Source dataset
uspto-grants-2012_04
Patent number
US08153823B2

Reaction notes

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