Lawesson's reagent → HCID 22623070, compound

HRID 840383Notes

Reaction equation

HRID 840383 reaction equation
[CH3:1][CH:2]1[C:7](=O)[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[CH:11]=[CH:12][C:4]=2[O:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:28])=CC=1>C(COC)OC>[CH3:1][CH:2]1[C:7](=[S:28])[NH:6][C:5]2[CH:9]=[C:10]([CH2:13][N:14]3[CH:18]=[CH:17][N:16]=[CH:15]3)[CH:11]=[CH:12][C:4]=2[O:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 22622957HCID 22622957, compound

Product 1

HCID 22623070HCID 22623070, compoundYield 57.4%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

390 mg (1.603 mmol) of (±)-2-methyl-3-oxo-6-[(1-imidazolyl)-methyl]-3,4-dihydro-2H-1,4-benzoxazine is dissolved in 42 ml of dimethoxyethane, mixed with 1.297 g (3.206 mmol) of Lawesson's reagent and stirred for 46 hours at room temperature. After the solvent is spun in, the residue is chromatographed on silica gel (mobile solvent: methylene chloride/ethanol). The fractions that are obtained by chromatography are removed from the polar contaminants by shaking with saturated sodium bicarbonate solution. 238.5 mg (57%) of the desired product is isolated, ting point 206-210° C.

Workup

  1. customis chromatographed on silica gel (mobile solvent: methylene chloride/ethanol)
  2. customThe fractions that are obtained by chromatography
  3. customare removed from the polar contaminants
  4. stirringby shaking with saturated sodium bicarbonate solution

Sources & evidence

ORD record
ord-17d42d45e2fe4af3b8844cc1df0137d3
Source dataset
uspto-grants-2002_04
Patent number
US06365736B1

Reaction notes

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