Lawesson's reagent → HCID 57475963, compound

HRID 1960247Notes

Reaction equation

HRID 1960247 reaction equation
[CH:1]([N:4]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14]([NH2:16])=O)=[CH:10]2)([CH3:3])[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1>O1CCCC1>[CH:1]([N:4]([S:17]([C:20]1[S:21][CH:22]=[CH:23][CH:24]=1)(=[O:19])=[O:18])[C:5]1[CH:6]=[CH:7][CH:8]=[C:9]2[C:13]=1[NH:12][C:11]([C:14](=[S:34])[NH2:16])=[CH:10]2)([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 57475958HCID 57475958, compound

Product 1

HCID 57475963HCID 57475963, compoundYield 74.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 7-[isopropyl(2-thienylsulfonyl)amino]-1H-indole-2-carboxamide (320 mg), Lawesson's reagent (213 mg) and tetrahydrofuran (5 ml) was stirred at 70° C. for 1 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from methylene chloride-toluene mixture, and washed with hexane to give the title compound (148 mg, yield 44%) as crystals. melting point 204-205° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from methylene chloride-toluene mixture
  3. washwashed with hexane

Sources & evidence

ORD record
ord-6e5fee9637b54046b58a9e789e50b863
Source dataset
uspto-grants-2013_04
Patent number
US08410087B2

Reaction notes

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