Methanol → HCID 66852048, compound

HRID 254666Notes

Reaction equation

HRID 254666 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][CH:9]1[CH2:12][CH2:11][CH2:10]1.C(Cl)Cl.C[OH:17]>>[NH4+:1].[OH-:17].[CH:9]1([CH2:8][N:6]2[CH:5]=[CH:4][S:3][C:2]2=[NH:1])[CH2:12][CH2:11][CH2:10]1

Participants

6

Reactant 4

HCID 887MethanolHCID 21552-AminothiazoleHCID 6344DichloromethaneHCID 2734658(Bromomethyl)cyclobutane

Product 2

HCID 14923Ammonium HydroxideHCID 66852048HCID 66852048, compoundYield 80%

Conditions

Temperature
85 °C

Procedure

A mixture of 2-aminothiazole (1.0 g, 10 mmol) and (bromomethyl)cyclobutane (1.1 mL, 10 mmol) was warmed to 85° C. and was allowed to stir for 18 h. The mixture was cooled to ambient temperature and the crude material was purified via column chromatography (SiO2, 10% MeOH in EtOAc then 9:1:0.1 CH2Cl2:MeOH:NH4OH) to provide the title compound (1.4 g, 8.0 mmol, 80% yield). MS (DCI/NH3) m/z 169 (M+H)+.

Workup

  1. temperatureThe mixture was cooled to ambient temperature
  2. customthe crude material was purified via column chromatography (SiO2, 10% MeOH in EtOAc

Sources & evidence

ORD record
ord-4d0d19113c5242f98938055c22e81ab6
Source dataset
uspto-grants-2011_01
Patent number
US07875640B2

Reaction notes

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