Benzenesulfonic Acid → HCID 57628288, compound

HRID 1692064Notes

Reaction equation

HRID 1692064 reaction equation
C1(S(O)(=O)=O)C=CC=CC=1.[NH2:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1/[C:17](=[CH:19]/[CH:20]([CH3:22])[CH3:21])/[CH3:18].NC1C=CSC=1/C(=C\C(C)C)/C>>[NH2:11][C:12]1[CH:16]=[CH:15][S:14][C:13]=1[C:17]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH2:18]

Participants

4

Reactant 3

HCID 7371Benzenesulfonic AcidHCID 44139031HCID 44139031, compoundHCID 57628287HCID 57628287, compound

Product 1

HCID 57628288HCID 57628288, compoundYield 80%

Procedure

Into a solution obtained by dissolving 3-aminothiophene (1.4 g, 14.5 mmol) in 4-methyl-2-pentanone (30.0 g), which was obtained in the same manner as in Example 14 using methyl 3-aminothiophene-2-carboxylate as a starting material was added anhydrous benzenesulfonic acid (4.7 g, 29.7 mmol) at room temperature, and the resulting solution was stirred under nitrogen atmosphere at 60 degree centigrade for 30 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, 2.1 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: 80%).

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. custom2.1 g was produced as a mixture of three compounds

Sources & evidence

ORD record
ord-bd7587608f6741aa98bcae4127ca9329
Source dataset
uspto-grants-2012_04
Patent number
US08153823B2

Reaction notes

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