Lawesson's reagent → HCID 86652387, compound

HRID 874772Notes

Reaction equation

HRID 874772 reaction equation
[Cl:1][C:2]1[CH:17]=[C:16]([N:18]2[CH2:22][CH2:21][C:20]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)([C:23]([F:26])([F:25])[F:24])[CH2:19]2)[CH:15]=[CH:14][C:3]=1[C:4]([NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:44])=CC=1>C1(C)C=CC=CC=1>[Cl:1][C:2]1[CH:17]=[C:16]([N:18]2[CH2:22][CH2:21][C:20]([C:27]3[CH:32]=[C:31]([Cl:33])[CH:30]=[C:29]([Cl:34])[CH:28]=3)([C:23]([F:26])([F:25])[F:24])[CH2:19]2)[CH:15]=[CH:14][C:3]=1[C:4](=[S:44])[NH:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 24948331HCID 24948331, compound

Product 1

HCID 86652387HCID 86652387, compoundYield 27.7%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To the solution of 2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin1-yl]-N-(pyridin-2-ylmethyl)benzamide (0.35 g) in toluene was added Lawesson reagent (0.28 g) and the mixture was heated to reflux for 3 hours. After the mixture was cooled to room temperature, the solvent was distilled away under the reduced pressure, and the residue was purified by silica gel chromatography to yield 2-chloro-4-[3-(3,5-dichlorophenyl)-3-(trifluoromethyl)pyrrolidin1-yl]-N-(pyridin-2-ylmethyl)benzenecarbothioamide (0.10 g). 1H-NMR (CDCl3) δ: 2.51-2.61 (1H, m), 2.84-2.92 (1H, m), 3.45-3.61 (2H, m), 3.79 (1H, d), 4.08 (1H, d), 5.08 (2H, d), 6.49-6.54 (2H, m), 7.22-7.28 (3H, m), 7.36 (1H, d), 7.40 (1H, t), 7.72 (1H, td), 7.79 (1H, d), 8.54 (1H, d), 9.27 (1H, br s).

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 3 hours
  3. distillationthe solvent was distilled away under the reduced pressure
  4. customthe residue was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9d81ddb67fb049a08f5b7e73a91f8105
Source dataset
uspto-grants-2015_03
Patent number
US08980937B2

Reaction notes

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