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

HRID 408833Notes

Reaction equation

HRID 408833 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 (1 H, 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-7eaf2e0f23d94fa7a31be1214a2b96db
Source dataset
uspto-grants-2014_06
Patent number
US08759361B2

Reaction notes

Loading…