Hexane → 4-(Phenylethynyl)-1,3-thiazol-2-amine

HRID 967742Notes

Reaction equation

HRID 967742 reaction equation
Cl[CH2:2][C:3](=O)[C:4]#[C:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[NH2:13][C:14]([NH2:16])=[S:15].CCCCCC>CN(C=O)C.C(OCC)(=O)C>[C:6]1([C:5]#[C:4][C:3]2[N:13]=[C:14]([NH2:16])[S:15][CH:2]=2)[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 8058HexaneHCID 2723790ThioureaHCID 110085031-chloro-4-phenyl-3-Butyn-2-one

Product 1

HCID 222913294-(Phenylethynyl)-1,3-thiazol-2-amineYield 20.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Procedure

1-Chloro-4-phenyl-3-butyn-2-one (245 mg, 1.37 mmol) was dissolved in DMF (1.0 mL), thiourea (126 mg, 1.66 mmol) was added, and the resulting pale brown solution was stirred at ambient temperature for 5 days. The reaction mixture was diluted with Ethyl acetate (50 mL), washed with saturated NaHCO3 solution (10 mL), water (10 mL), brine (10 mL), dried over Na2SO4, filtered, and concentrated in vacuo. The dark oil was dissolved in methanol, adsorbed onto silica gel and purified by column chromatography eluting with 4:1, 3:1, then 2:1 hexane:ethyl acetate to afford 4-(phenylethynyl)-1,3-thiazol-2-amine (56 mg, 20% yield) as an oil. 1H NMR (CDCl3, 300 MHz) δ 7.53–7.50 (m, 2H), 7.37–7.32 (m, 3H), 6.77 (s, 1H), 5.41 (br s, 2H). MS (EI ionization) 200 (M+).

Workup

  1. washwashed with saturated NaHCO3 solution (10 mL), water (10 mL), brine (10 mL)
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. dissolutionThe dark oil was dissolved in methanol
  6. custompurified by column chromatography
  7. washeluting with 4:1, 3:1

Sources & evidence

ORD record
ord-47cce72f97cd4e0087d32a7cb0dace4a
Source dataset
uspto-grants-2005_10
Patent number
US06956049B1

Reaction notes

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