Lawesson's reagent → HCID 86642127, compound

HRID 641441Notes

Reaction equation

HRID 641441 reaction equation
[CH3:1][C:2]1([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:36])=CC=1>>[CH3:1][C:2]1([CH2:21][C:22]([O:24][CH2:25][CH3:26])=[O:23])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:3]1=[S:36]

Participants

3

Reactant 2

HCID 87949Lawesson's reagentHCID 66636581HCID 66636581, compound

Product 1

HCID 86642127HCID 86642127, compound

Procedure

A mixture of (±)-diethyl 2,2′-(3-methyl-4-nitro-2-oxo-2,3-dihydro-1H-indole-1,3-diyl)diacetate from Step B (2.30 g, 6.31 mmol) and Lawesson's reagent (1.53 g, 3.79 mmol) was heated at 150° C. in xylenes (120 mL) for 18 h. The reaction mixture was concentrated in vacuo and the residue was purified by silica gel chromatography, eluting with a gradient of hexane:EtOAc—100:0 to 0:100, to give the title compound. MS: m/z=381 (M+1).

Workup

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

Sources & evidence

ORD record
ord-f373f75292944a73b633c2f5be67e7d8
Source dataset
uspto-grants-2010_04
Patent number
US07696192B2

Reaction notes

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