2-Aminothiazole → 1-methyl-1H-pyrrole-2-ethylamine

HRID 2257767Notes

Reaction equation

HRID 2257767 reaction equation
[N-:1]=[C:2]=[S:3].NC1S[CH:7]=[CH:8][N:9]=1.CCO[C:13]([CH3:15])=O.[CH3:16][N:17]([CH:19]=O)[CH3:18]>>[N-:1]=[C:2]=[S:3].[NH2:9][CH2:8][CH2:7][C:19]1[N:17]([CH3:18])[CH:16]=[CH:13][CH:15]=1

Participants

6

Reactant 4

HCID 21552-AminothiazoleHCID 6228DimethylformamideHCID 8857Ethyl AcetateHCID 178418790HCID 178418790, compound

Product 2

HCID 5650581-methyl-1H-pyrrole-2-ethylamineHCID 178418790HCID 178418790, compound

Conditions

Temperature
100 °C

Procedure

An isothiocyanate of 2-(2-aminoethyl)-1-methylpyrrole was prepared according to Ann 657, 104-107 (1962). 1H-NMR (CDCl3) δ 2.95 (t, 2H), 3.55 (s, 1H), 3.65 (t, 2H), 5.9-5.95 (m, 1H), 6.05 (t, 1H), 6.55 (t, 1H). This isothiocyanate was dissolved in DMF (4 ml). To this solution was added 200 mg (2 mmol) of 2-aminothiazole and the solution was heated at 100° C. for about 16 h. EtOAc was added and the organic phase was washed with sat. NH4Cl-solution and brine. After drying (Na2SO4), the product was purified on a silica gel column, using EtOAc/Hexane 1:1, as eluent. This gave almost pure titled product. Recrystallization from toluene/hexanes gave 150 mg of the titled product.

Workup

  1. washthe organic phase was washed with sat. NH4Cl-solution and brine
  2. dry with materialAfter drying (Na2SO4)
  3. customthe product was purified on a silica gel column

Sources & evidence

ORD record
ord-d0dca7a785654987b3bef99822a1c63e
Source dataset
uspto-grants-1997_08
Patent number
US05658907

Reaction notes

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