4-Iodobenzoyl chloride → Benzenecarbothioic acid, 4-iodo-, S-2-pyridinyl ester

HRID 584098Notes

Reaction equation

HRID 584098 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](Cl)=[O:7])=[CH:4][CH:3]=1.[SH:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=1>C1COCC1>[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6](=[O:7])[S:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][N:13]=2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 743734-Iodobenzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 10593305Benzenecarbothioic acid, 4-iodo-, S-2-pyridinyl ester

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the general procedure described above, reaction of 4-iodobenzoyl chloride (8.01 g, 30.0 mmol) with 2-mercaptopyridine (3.33 g, 30.0 mmol) in THF (60 mL) for 30 min at room temperature afforded pale yellow solid after precipitation (9.61 g, 94%): mp 127° C.; 1H NMR δ 7.30-7.38 (m, 1H), 7.70-7.76 (m, 3H), 7.77-7.83 (m, 1H), 7.84-7.89 (m, 2H), 8.64-8.71 (m, 1H); Anal. Calcd for C12H8INOS: C, 42.25; H, 2.36; N, 4.11. Found: C, 42.27; H, 2.38; N, 4.05.

Workup

  1. customafforded pale yellow solid
  2. customafter precipitation (9.61 g, 94%)

Sources & evidence

ORD record
ord-6c139e2ff96a4a8f894de2b72e4ce311
Source dataset
uspto-grants-2005_08
Patent number
US06924375B2

Reaction notes

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