Pentafluorobenzoyl chloride → S-2-Pyridyl pentafluorobenzothioate

HRID 584097Notes

Reaction equation

HRID 584097 reaction equation
[F:1][C:2]1[C:7]([C:8](Cl)=[O:9])=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14].[SH:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=1>C1COCC1>[F:1][C:2]1[C:7]([C:8](=[O:9])[S:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][N:17]=2)=[C:6]([F:11])[C:5]([F:12])=[C:4]([F:13])[C:3]=1[F:14]

Participants

4

Reactant 2

HCID 75256Pentafluorobenzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 10494768S-2-Pyridyl pentafluorobenzothioate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure described above, reaction of pentafluorobenzoyl chloride (6.92 g, 30.0 mmol) with 2-mercaptopyridine (3.33 g, 30.0 mmol) in THF (30 mL) for 30 min at room temperature afforded pale yellow solid after precipitation (7.97 g, 87%): mp 51° C.; 1H NMR δ 7.37-7.42 (m, 1H), 7.75-7.79 (m, 1H), 7.81-7.87 (m, 1H), 8.67-8.71 (m, 1H); Anal. Calcd for C12H4NOS: C, 47.22; H, 1.32; N, 4.59. Found: C, 47.59; H, 1.29; N, 4.38.

Workup

  1. customafforded pale yellow solid
  2. customafter precipitation (7.97 g, 87%)

Sources & evidence

ORD record
ord-5411c09e69ae423ca87bd6978a0f548b
Source dataset
uspto-grants-2005_08
Patent number
US06924375B2

Reaction notes

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