Lawesson's reagent → HCID 86666723, compound

HRID 2401384Notes

Reaction equation

HRID 2401384 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:25]([CH3:26])=[C:24]([CH3:27])[S:23][C:10]=3[C:11]3[C:21]([CH3:22])=[N:20][O:19][C:12]=3[C@H:13]([CH2:15][C:16]([NH2:18])=O)[N:14]=2)=[CH:4][CH:3]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:37])=CC=1>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9]3[C:25]([CH3:26])=[C:24]([CH3:27])[S:23][C:10]=3[C:11]3[C:21]([CH3:22])=[N:20][O:19][C:12]=3[C@H:13]([CH2:15][C:16](=[S:37])[NH2:18])[N:14]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57345400HCID 57345400, compound2×

Product 1

HCID 86666723HCID 86666723, compoundYield 64.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)acetamide (Compound 110, 0.120 g, 0.30 mmol) in THF (5 mL) was added Lawesson reagent (0.248 g, 0.60 mmol). The mixture was refluxed overnight. The reaction mixture was concentrated in vacuo and the residue was recrystallized by petroleum and ethyl acetate to give 2-((6S)-4-(4-chlorophenyl)-2,3,9-trimethyl-6H-isoxazolo[5,4-c]thieno[2,3-e]azepin-6-yl)ethanethioamide (0.080 g, 64% yield).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was recrystallized by petroleum and ethyl acetate

Sources & evidence

ORD record
ord-9bffb64e27df46a0a5f69554b1507ccf
Source dataset
uspto-grants-2014_08
Patent number
US08796261B2

Reaction notes

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