Ammonia → 4-(2,3-Dihydroimidazo[2,1-b]thiazol-5-yl)benzonitrile

HRID 2053778Notes

Reaction equation

HRID 2053778 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=1)=O.[NH2:13][C:14]1[S:15][CH2:16][CH2:17][N:18]=1.Cl.N>C(#N)C.CO>[S:15]1[CH2:16][CH2:17][N:18]2[C:3]([C:5]3[CH:12]=[CH:11][C:8]([C:9]#[N:10])=[CH:7][CH:6]=3)=[CH:2][N:13]=[C:14]12

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 156894,5-Dihydro-2-thiazolamineHCID 986544-(Bromoacetyl)benzonitrile

Product 1

HCID 693096964-(2,3-Dihydroimidazo[2,1-b]thiazol-5-yl)benzonitrile

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6342AcetonitrileSolvent

Procedure

3.00 g (12.72 mmol) of 4-bromoacetylbenzonitrile is dissolved in 40 mL acetonitrile, and combined with 2.65 g (25.42 mmol) of 2-amino-4,5-dihydrothiazole and 2.00 g of molecular sieve 4 Å. Then the mixture is stirred for 2.5 days at ambient temperature. Then the solvent is eliminated in vacuo, and the residue is taken up with 100 mL of 1 molar hydrochloric acid solution and the insoluble matter is taken up with a little methanol and concentrated ammonia solution. After filtration, the filtrate is concentrated in vacuo and purified by chromatography on silica gel (gradient: initially ethyl acetate/ethanol=100:0 □40:60+0.5% ammonia, then dichloromethane/methanol=6:4+2% triethylamine). Yield: 2.4 g; Rf value: 0.65 (silica gel; ethyl acetate/ethanol=8:2+1% ammonia); C12H9N3S (227.29); mass spectrum: (M+H)+=228

Workup

  1. filtrationAfter filtration
  2. concentrationthe filtrate is concentrated in vacuo
  3. custompurified by chromatography on silica gel (gradient

Sources & evidence

ORD record
ord-74fa53b0f0e8403083f0cde1f9563c67
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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