3,5-Di-t-butylbenzoyl chloride → S-2-Pyridyl 3,5-di-tert-butylbenzothioate

HRID 496848Notes

Reaction equation

HRID 496848 reaction equation
[SH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.[C:8]([C:12]1[CH:13]=[C:14]([CH:18]=[C:19]([C:21]([CH3:24])([CH3:23])[CH3:22])[CH:20]=1)[C:15](Cl)=[O:16])([CH3:11])([CH3:10])[CH3:9]>C(Cl)Cl>[C:21]([C:19]1[CH:18]=[C:14]([CH:13]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[CH:20]=1)[C:15](=[O:16])[S:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1)([CH3:24])([CH3:23])[CH3:22]

Participants

4

Reactant 2

HCID 118176223,5-Di-t-butylbenzoyl chlorideHCID 178418616HCID 178418616, compound

Product 1

HCID 11088731S-2-Pyridyl 3,5-di-tert-butylbenzothioate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a stirred solution of 2-mercaptopyridine (2.78 g, 25.0 mmol) in CH2Cl2 (50 mL) was added a solution of 3,5-di-tert-butylbenzoyl chloride (6.31 g, 25.0 mmol) in CH2Cl2 (125 mL) over 10 min. After 5 h, TLC showed complete consumption of the 2-mercaptopyridine, then 2 N NaOH was added The organic phase was isolated, washed with water, then dried (Na2SO4) and the solvent was removed to afford a white solid. The solid was recrystallized in hexane affording a white solid (5.05 g, 62%): mp 73-74°°C.; 1H NMR δ 1.36 (s, 18H), 7.31-7.36 (m, 1H), 7.67-7.70 (m, 1H), 7.75-7.80 (m, 2H), 7.85-7.88 (m, 2H), 8.66-8.69 (m, 1H); 13C NMR δ 32.0, 35.7, 122.6, 124.2, 128.9, 131.4, 136.9, 137.7, 151.1, 152.3, 152.5, 190.8; Anal. Calcd for C20H25NOS: C, 73.35; H, 7.69; N, 4.28. Found: C, 73.40; H, 7.75; N, 4.23.

Workup

  1. customconsumption of the 2-mercaptopyridine
  2. addition2 N NaOH was added The organic phase
  3. customwas isolated
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. customthe solvent was removed
  7. customto afford a white solid
  8. customThe solid was recrystallized in hexane affording a white solid (5.05 g, 62%)

Sources & evidence

ORD record
ord-a3307bd40b814712bedfe3088e4f2c7f
Source dataset
uspto-grants-2005_09
Patent number
US06946552B2

Reaction notes

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