Lawesson's reagent → Ethyl 5-amino-1,3-thiazole-4-carboxylate

HRID 1674708Notes

Reaction equation

HRID 1674708 reaction equation
[CH:1]([NH:3][C@H:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[C:5]#[N:6])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:21])=CC=1>C1C=CC=CC=1>[NH2:6][C:5]1[S:21][CH:1]=[N:3][C:4]=1[C:7]([O:9][CH2:10][CH3:11])=[O:8]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 86619658Ethyl N-formyl-3-nitriloalaninate

Product 1

HCID 12620181Ethyl 5-amino-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

Ethyl N-formyl-3-nitriloalaninate (11.22 g, 71.86 mmol) is dissolved in anhydrous benzene (220 mL). Following the addition of Lawesson's reagent (14.53 g, 35.93 mmol), the suspension is refluxed for 24 h. Most of the solvent is removed in vacuo, and the viscous red residue is absorbed on silica gel and loaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50). The title compound is obtained as yellow solids. 1H NMR (400 MHz, CDCl3) 7.87 (1H, s), 7.26 (1H, s), 6.01 (2H, broad s), 4.38 (2H, q), 1.41 (3H, t).

Workup

  1. temperaturethe suspension is refluxed for 24 h
  2. customMost of the solvent is removed in vacuo
  3. customthe viscous red residue is absorbed on silica gel
  4. washloaded to a silica gel column (elution solvent: EtOAc:hexanes=50:50)

Sources & evidence

ORD record
ord-50dbc6b5bfcb457abdce22272d52d9a6
Source dataset
uspto-grants-2011_08
Patent number
US08003656B2

Reaction notes

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