Toluene → HCID 86622680, compound

HRID 1441271Notes

Reaction equation

HRID 1441271 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18]([NH2:20])=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1.C1(C)C=CC=CC=1>O1CCCC1>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:10]=1[N:9]([CH2:11][CH:12]1[CH2:17][CH2:16][O:15][CH2:14][CH2:13]1)[CH:8]=[C:7]2[C:18](=[S:30])[NH2:20]

Participants

5

Reactant 3

HCID 1140TolueneHCID 87949Lawesson's reagentHCID 68538635HCID 68538635, compound

Product 1

HCID 86622680HCID 86622680, compoundYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carboxylic acid amide (1.8 g, 6.0 mmol), Lawesson's reagent (4.85 g, 12.0 mmol), toluene (150 ml) and tetrahydrofuran (50 ml) was stirred at room temperature for 3 days. The reaction mixture was concentrated in vacuo and the obtained reside was purified by column chromatography eluting with 20-50% (v/v) ethyl acetate in n-heptane to afford 7-chloro-1-(tetrahydropyran-4-yl)methyl-1H-indole-3-carbothioic acid amide (1.4 g, 4.5 mmol).

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe obtained reside was purified by column chromatography
  3. washeluting with 20-50% (v/v) ethyl acetate in n-heptane

Sources & evidence

ORD record
ord-08195b4f6e0f46d8a701a9f2b0ac349c
Source dataset
uspto-grants-2010_02
Patent number
US07655645B2

Reaction notes

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