Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate → HCID 58121076, compound

HRID 1186707Notes

Reaction equation

HRID 1186707 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:6]=1.Br[CH2:19][C:20]([C:22]1[CH:23]=[C+:24][CH:25]=[CH:26][CH:27]=1)=O>C(O)CCC.[Cl-].[Na+].O>[C:7]1([C:5]2[N:6]3[CH:19]=[C:20]([C:22]4[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=4)[N:1]=[C:2]3[S:3][C:4]=2[C:13]([O:15][CH2:16][CH3:17])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateHCID 21362836HCID 21362836, compound

Product 1

HCID 58121076HCID 58121076, compoundYield 18.3%

Reagents, catalysts & solvents 2

HCID 2631-ButanolSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A solution of ethyl 2-amino-4-phenylthiazole-5-carboxylate 93 (0.7 g, 2.82 mmol) and 3-(2-bromoacetyl)benzene-1-ylium 68 (0.34 mL, 2.82 mmol) was stirred at 120° C. in butanol (9 mL) for 3 d. The solution was cooled to room temperature, diluted with brine and extracted with ethyl acetate. The combined organics were dried over Na2SO4, filtered and concentrated under reduced pressure to afford ethyl 3,6-diphenylimidazo[2,1-b]thiazole-2-carboxylate 94 (0.18 g, 18% yield) as a tan solid after purification by flash chromatography (0 to 30% MeOH in ethyl acetate) followed by trituration in hexane. LRMS (ESI): (calc) 348.42 (found) 349.2 (MH)+

Workup

  1. extractionextracted with ethyl acetate
  2. dry with materialThe combined organics were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-8427a942f2804a938f6f43d198cd68ec
Source dataset
uspto-grants-2014_03
Patent number
US08673911B2

Reaction notes

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