Lawesson's reagent → HCID 86643630, compound

HRID 2061868Notes

Reaction equation

HRID 2061868 reaction equation
[Br:1][C:2]1[C:3]([C:16](=O)[NH2:17])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>O1CCCC1>[Br:1][C:2]1[C:3]([C:16](=[S:28])[NH2:17])=[CH:4][C:5]([NH:8][C:9](=[O:15])[O:10][C:11]([CH3:14])([CH3:13])[CH3:12])=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 67029027HCID 67029027, compound2×

Product 1

HCID 86643630HCID 86643630, compoundYield 97.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The crude tert-butyl 5-bromo-4-carbamoylpyridin-2-ylcarbamate (Intermediate 84, 232 mmol) was treated with Lawesson's Reagent (94 g, 232 mmol, 1 eq) and tetrahydrofuran (700 mL), the resulting mixture was heated at reflux for 1 h, then it was allowed to stir at room temperature over the weekend. The mixture was concentrated to dryness in vacuo and toluene (˜300 mL) was added. A bright yellow solid precipitated formed which was collected by filtration and washed with toluene, then dried in the vacuum oven at 50° C. for 4 h, yielding 75 g of a bright yellow solid (97%).

Workup

  1. temperaturethe resulting mixture was heated
  2. temperatureat reflux for 1 h
  3. concentrationThe mixture was concentrated to dryness in vacuo and toluene (˜300 mL)
  4. additionwas added
  5. customA bright yellow solid precipitated
  6. customformed which
  7. filtrationwas collected by filtration
  8. washwashed with toluene
  9. customdried in the vacuum oven at 50° C. for 4 h

Sources & evidence

ORD record
ord-7ee22519fe2d4c7293ab9e4725767b91
Source dataset
uspto-grants-2012_10
Patent number
US08283361B2

Reaction notes

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