Ethyl benzoylacetate → Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylate

HRID 610120Notes

Reaction equation

HRID 610120 reaction equation
[C:1]1([C:7](=O)[CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.OC1C(OS(C2C=CC(C)=CC=2)(=O)=O)=C(I)C=CC=1.[NH2:34][C:35]([NH2:37])=[S:36]>C(#N)C>[NH2:37][C:35]1[S:36][C:8]([C:9]([O:11][CH2:12][CH3:13])=[O:10])=[C:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[N:34]=1

Participants

5

Reactant 3

HCID 7170Ethyl benzoylacetateHCID 2723790ThioureaHCID 21918218Hydroxy tosyloxy iodobenzene

Product 1

HCID 73239Ethyl 2-amino-4-phenyl-1,3-thiazole-5-carboxylateYield 75.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
65 °C

Procedure

To a solution of ethyl 3-phenyl-3-oxopropionate (5.0 g, 26.0 mmol) in 100 mL of acetonitrile was added hydroxy(tosyloxy)iodobenzene (11.2 g, 28.6 mmol) . The resulting suspension was stirred at 65° C. for 1 h at which time the reaction was a homogeneous solution. Thiourea (2.2 g, 28.6 mmol) was added and stirring was continued at 65° C. for 2 h. The mixture was cooled and concentrated, and the residue was taken up in ethyl acetate, washed with saturated aq Na2CO3 and brine, dried (MgSO4) and concentrated. The residue was triturated with ethyl ether to afford 4.9 g (70%) of the title compound as a yellow solid. 1H NMR (CDCl3) d 7.65 (m, 2H), 7.39 (m, 3H), 5.98 (broad s, 2H), 4.18 (q, 2H), 1.22 (t, 3H).

Workup

  1. stirringstirring
  2. waitwas continued at 65° C. for 2 h
  3. temperatureThe mixture was cooled
  4. concentrationconcentrated
  5. washwashed with saturated aq Na2CO3 and brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customThe residue was triturated with ethyl ether

Sources & evidence

ORD record
ord-519cc44bacb64eeea840e2123754ed53
Source dataset
uspto-grants-1999_12
Patent number
US05998424

Reaction notes

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