2-Aminothiazole → HCID 66966772, compound

HRID 1366238Notes

Reaction equation

HRID 1366238 reaction equation
[Br:1][C:2]1[S:6][C:5]([CH:7]=O)=[CH:4][CH:3]=1.[C:9]([N+:13]#[C-:14])([CH3:12])([CH3:11])[CH3:10].[NH2:15][C:16]1[S:17][CH:18]=[CH:19][N:20]=1.Cl(O)(=O)(=O)=O.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)(Cl)Cl.C(Cl)Cl>[Br:1][C:2]1[S:6][C:5]([C:7]2[N:15]=[C:16]3[N:20]([C:14]=2[NH:13][C:9]([CH3:12])([CH3:11])[CH3:10])[CH:19]=[CH:18][S:17]3)=[CH:4][CH:3]=1

Participants

8

Reactant 5

HCID 21552-AminothiazoleHCID 10340Sodium CarbonateHCID 23577Tert-Butyl isocyanideHCID 24247Perchloric AcidHCID 784285-Bromothiophene-2-carbaldehyde

Product 1

HCID 66966772HCID 66966772, compoundYield 15.4%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

22.9 g (119.9 mmol) 5-bromo-thiophene-2-carbaldehyde and 11.0 g (131.9 mmol) tert.-butyl-isonitrile were added to a solution of 12.0 g (119.9 mmol) 2-amino-thiazole in chloroform (60 ml). A 1 molar perchloric acid (2.3 ml) was added to the reaction solution and heated to 50° C. while being stirred for 5 d. After cooling to RT, dilution with DCM was performed and a 1 molar aq. Na2CO3 sol. added. After 10 min of stirring at RT, the phases were separated. The organic phase was dried over Na2SO4, filtered and concentrated in a vacuum. 6.6 g (18.5 mmol, 15%) 6-(5-bromothiophene-2-yl)-N-tert-butylimidazo[2,1-b]thiazole-5-amine ([MH+] 356.0) was obtained by crystallisation of the residue from AE.

Workup

  1. temperatureAfter cooling to RT
  2. stirringAfter 10 min of stirring at RT
  3. customthe phases were separated
  4. dry with materialThe organic phase was dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in a vacuum

Sources & evidence

ORD record
ord-6e9c5dbe05704565927b9610478ba902
Source dataset
uspto-grants-2011_02
Patent number
US07893069B2

Reaction notes

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