Lawesson's reagent → Ethyl 5-amino-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylate

HRID 705225Notes

Reaction equation

HRID 705225 reaction equation
[C:1]([CH:3]([NH:9][C:10](=O)[C:11]1[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=1[F:18])[C:4]([O:6][CH2:7][CH3:8])=[O:5])#[N:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>N1C=CC=CC=1>[NH2:2][C:1]1[S:29][C:10]([C:11]2[C:16]([F:17])=[CH:15][CH:14]=[CH:13][C:12]=2[F:18])=[N:9][C:3]=1[C:4]([O:6][CH2:7][CH3:8])=[O:5]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 59455767Ethyl 2-cyano-2-(2,6-difluorobenzamido)acetate

Product 1

HCID 66652898Ethyl 5-amino-2-(2,6-difluorophenyl)-1,3-thiazole-4-carboxylateYield 25%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of the ethyl 2-cyano-2-(2,6-difluorobenzamido)acetate (1 eq) in pyridine (0.1 M) was added Lawesson's reagent (1.5 eq.). The mixture was stirred at reflux under Ar for 18 hours. Solvents were removed under reduced pressure. The crude residue was purified by flash chromatography (EtOAc:hexanes=1:1) to give the ethyl 5-amino-2-(2,6-difluorophenyl)thiazole-4-carboxylate in 25% yield. LC/MS (m/z): 284.9 (MH+), Rt: 0.76 min.

Workup

  1. temperatureat reflux under Ar for 18 hours
  2. customSolvents were removed under reduced pressure
  3. customThe crude residue was purified by flash chromatography (EtOAc:hexanes=1:1)

Sources & evidence

ORD record
ord-99acd3e6fe2e44d2b1d48aa68cd6b158
Source dataset
uspto-grants-2015_11
Patent number
US09173883B2

Reaction notes

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