2-Aminothiazole → HCID 3758127, compound

HRID 1783801Notes

Reaction equation

HRID 1783801 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=1)=O.[OH-].[NH4+]>C(O)C>[CH3:18][O:17][C:13]1[CH:12]=[C:11]([C:9]2[N:1]=[C:2]3[N:6]([CH:8]=2)[CH:5]=[CH:4][S:3]3)[CH:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 14923Ammonium HydroxideHCID 101294Bromomethyl 3-methoxyphenyl ketone

Product 1

HCID 3758127HCID 3758127, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-aminothiazole (2.7 g, 26.7 mmol) and 2-bromo-3′-methoxyacetophenone (6.0 g, 0.0262 mol) was added absolute ethanol (100 ml). The reaction was allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture was reduced to half its original volume in vacuo. The remaining liquid was poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%). The resulting fine solid was filtered and washed with water resulting in a dark yellow solid product. The solid product was dried in a vacuum oven at 50° C. to provide 6-(3-methoxyphenyl)-imidazo[2,1-b]thiazole (5.0 g, 81%). 400 MHz 1H NMR (DMSO-d6) δ 8.18 (s, 1H), 7.88 (d, J=4.4 Hz, 1H), 7.36-7.42 (m, 2H), 7.28 (t, J=8.1 Hz, 1H), 7.22 (d, J=4.4 Hz, 1H), 6.82 (ddd, J=8.1, 2.6, 1.1 Hz, 1H), 3.80 (s, 3H). LCMS: 231 [M+H].

Workup

  1. temperatureto reflux
  2. additionThe remaining liquid was poured onto ice
  3. filtrationThe resulting fine solid was filtered
  4. washwashed with water resulting in a dark yellow solid product
  5. customThe solid product was dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-ddbc6e5a49d544f9a50fc63ba8bdaf1c
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

Loading…