Methanol → 3-(3-(1H-pyrrol-1-yl)propyl)-5-methylthiazol-2(3H)-imine

HRID 2196809Notes

Reaction equation

HRID 2196809 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH3:7])=[CH:5][N:6]=1.Br[CH2:9][CH2:10][CH2:11][N:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.C(Cl)Cl.C[OH:21]>>[NH4+:1].[OH-:21].[N:12]1([CH2:11][CH2:10][CH2:9][N:6]2[CH:5]=[C:4]([CH3:7])[S:3][C:2]2=[NH:1])[CH:16]=[CH:15][CH:14]=[CH:13]1

Participants

6

Reactant 4

HCID 887MethanolHCID 6344DichloromethaneHCID 3517702-Amino-5-methylthiazoleHCID 5571191-(3-Bromopropyl)pyrrole

Product 2

HCID 14923Ammonium HydroxideHCID 666608383-(3-(1H-pyrrol-1-yl)propyl)-5-methylthiazol-2(3H)-imineYield 81%

Conditions

Temperature
85 °C

Procedure

A mixture of 2-amino-5-methylthiazole (0.55 g, 4.8 mmol) and 1-(3-bromopropyl)pyrrole (TCI-US, 1.0 g, 5.3 mmol) was warmed to 85° C. and was stirred for 2 h. The mixture was then cooled to ambient temperature and was purified by flash column chromatography (SiO2, 10% CH3OH in ethyl acetate then 9:1:0.1 CH2Cl2:CH3OH:NH4OH) to give the title compound (0.86 g, 3.9 mmol, 81% yield). MS (DCI/NH3) m/z 222 (M+NH4)+.

Workup

  1. temperatureThe mixture was then cooled to ambient temperature
  2. customwas purified by flash column chromatography (SiO2, 10% CH3OH in ethyl acetate

Sources & evidence

ORD record
ord-45ce09d6f2964b038393ac1b32e853e8
Source dataset
uspto-grants-2012_12
Patent number
US08338467B2

Reaction notes

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