Lawesson's reagent → HCID 14810917, compound

HRID 1710104Notes

Reaction equation

HRID 1710104 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11]([NH2:13])=O)=[CH:3]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:23])=CC=1>C1(C)C=CC=CC=1>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:11](=[S:23])[NH2:13])=[CH:3]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 8231871-methyl-1H-indole-3-carboxamide

Product 1

HCID 14810917HCID 14810917, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1-Methylindole-3-carboxamide (0.6 g) was suspended in toluene (20 ml); Lawesson's Reagent (0.7 g) was added and the mixture was heated at reflux under nitrogen for 30 min until dissolution occurred. The solution was cooled and toluene was removed under reduced pressure. The orange residue was purified by column chromatography on alumina using CH2Cl2 as eluant. This afforded an orange crystalline material, (0.5 g). δH (360 MHz, DMSO-d6) 3.82 (3H, s, NCH3), 7.18 and 7.23 (2H, 2×dt, J=7.1, 1.1 Hz, H-5 and H-6), 7.49 (1H, d, J=7.5 Hz, H-7), 8.08 (1H, s, H-2), 8.59 (1H, d, J=7.5 Hz, H-4), 8.76 (2H, brs, NH2); m/z 190 (M+, 100%), 174 (20), 157 (80).

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux under nitrogen for 30 min until dissolution
  3. temperatureThe solution was cooled
  4. customtoluene was removed under reduced pressure
  5. customThe orange residue was purified by column chromatography on alumina
  6. customThis afforded an orange crystalline material, (0.5 g)

Sources & evidence

ORD record
ord-4fd312858ead4ab9908f1a738ce1c843
Source dataset
uspto-grants-1990_08
Patent number
US04952587

Reaction notes

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