2-Aminothiazole → Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylate

HRID 1882128Notes

Reaction equation

HRID 1882128 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[CH:5][N:6]=1.Cl[CH:8]([C:14]([CH3:16])=O)[C:9]([O:11][CH2:12][CH3:13])=[O:10]>C(O)C>[CH3:16][C:14]1[N:1]=[C:2]2[N:6]([C:8]=1[C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:5]=[CH:4][S:3]2

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 11858Ethyl 2-chloroacetoacetate

Product 1

HCID 671011Ethyl 6-methylimidazo[2,1-b]thiazole-5-carboxylateYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-aminothiazole (5.0 g. 49.931 mmol) and ethyl 2-chloroacetoacetate (11.5 g, 69.965 mmol) in absolute ethanol (50 mL) was refluxed for 24 h under stirring. The solvent was evaporated under vacuum and the residue was triturated with water (150 mL). The resulting solid was filtered, and dried to give crude product which was further purified by column chromatography to give 3.15 g of the product as an off-white solid; 1H NMR (300 MHz, CDCl3) δ 1.41 (t, J=6.9 Hz, 3H), 2.61 (s, 3H), 4.38 (q, J=6.6 Hz, 2H), 7.41 (d, J=4.2 Hz, 1H), 8.05 (d, J=4.5 Hz, 1H); ESI-MS (m/z) 211.30 (MH)+.

Workup

  1. temperaturewas refluxed for 24 h
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was triturated with water (150 mL)
  4. filtrationThe resulting solid was filtered
  5. customdried
  6. customto give crude product which
  7. customwas further purified by column chromatography

Sources & evidence

ORD record
ord-d761285678d04e1398324029f79ce0dd
Source dataset
uspto-grants-2012_11
Patent number
US08318928B2

Reaction notes

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