2-Aminothiazole → HCID 57433652, compound

HRID 1783831Notes

Reaction equation

HRID 1783831 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]([C:17]#[N:18])[CH:12]=1)=O.[OH-].[NH4+]>C(O)C>[C: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)#[N:18]

Participants

5

Reactant 3

HCID 21552-AminothiazoleHCID 14923Ammonium HydroxideHCID 27358673-(2-Bromoacetyl)benzonitrile

Product 1

HCID 57433652HCID 57433652, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a mixture of 2-aminothiazole (3.29 g, 32.9 mmol) and 2-bromo-3′-cyano-acetophenone (7.37 g, 32.9 mmol) was added absolute ethanol (250 mL). The reaction was allowed to reflux with vigorous stirring for 20 hours. The reaction mixture was reduced to half its original volume in vacuo. The remaining suspension was poured onto ice-water (200 mL) and the resulting mixture was basified by addition of ammonium hydroxide solution (30%, 100 mL). Product was collected by filtration and washed with water (50 mL), dried in a vacuum oven at 50° C. to provide 6-(3-cyanophenyl)-imidazo[2,1-b]thiazole (6.0 g, 81%). It was used with out further purification. LCMS: 226 [M+H].

Workup

  1. temperatureto reflux
  2. additionThe remaining suspension was poured onto ice-water (200 mL)
  3. filtrationProduct was collected by filtration
  4. washwashed with water (50 mL)
  5. customdried in a vacuum oven at 50° C.

Sources & evidence

ORD record
ord-d81fd74075da410cb9bfee6494225657
Source dataset
uspto-grants-2009_03
Patent number
US07501430B2

Reaction notes

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