2-Aminothiazole → HCID 3758127, compound

HRID 1925216Notes

Reaction equation

HRID 1925216 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, 0.0267 mol) and 2-bromo-3′-methoxyacetophenone (6.0 g, 0.0262 mol) is added absolute ethanol (100 ml). The reaction is allowed to reflux with vigorous stirring for 18 hours (checked by HPLC). The reaction mixture is reduced to half its original volume in vacuo. The remaining liquid is poured onto ice and the solution made basic by the addition of ammonium hydroxide solution (30%). The resulting fine solid is filtered and washed with water resulting in a dark yellow solid product. The solid product is 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 is poured onto ice
  3. filtrationThe resulting fine solid is filtered
  4. washwashed with water resulting in a dark yellow solid product
  5. customThe solid product is dried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-6292f06e27ce449bba19cd066195301a
Source dataset
uspto-grants-2012_05
Patent number
US08178672B2

Reaction notes

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