Lawesson's reagent → (+/-)-Ethyl (3-methyl-4-nitro-2-thioxo-2,3-dihydro-1H-indol-3-yl)acetate

HRID 551012Notes

Reaction equation

HRID 551012 reaction equation
[CH3:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>>[CH3:1][C:2]1([CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][C:3]1=[S:30]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 86629726(-)-Ethyl (3-methyl-4-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate2×

Product 1

HCID 86629730(+/-)-Ethyl (3-methyl-4-nitro-2-thioxo-2,3-dihydro-1H-indol-3-yl)acetate

Procedure

A mixture of (±)-ethyl (3-methyl-4-nitro-2-oxo-2,3-dihydro-1H-indol-3-yl)acetate (1.08 g, 3.88 mmol, described in Intermediate 17) and Lawesson's reagent (942 mg, 2.33 mmol) was heated at reflux in xylenes (30 mL) for 90 min. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:EtOAc—100:0 to 90:10, to give the title compound. MS: m/z=295 (M+1).

Workup

  1. temperaturewas heated
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customthe residue was purified by silica gel chromatography
  4. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-74593b61ff6248cd991381909d1e349a
Source dataset
uspto-grants-2011_05
Patent number
US07947677B2

Reaction notes

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