Triethylamine → 4-(2-(Isoindolin-1-on-2-yl)ethylthio]pyridine

HRID 6153Notes

Reaction equation

HRID 6153 reaction equation
O[CH2:2][C:3]1[CH:20]=[CH:19][CH:18]=[CH:17][C:4]=1[C:5]([NH:7][CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=[O:6].C(N(CC)CC)C.CS(Cl)(=O)=O>C(Cl)Cl>[C:5]1(=[O:6])[C:4]2[C:3](=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:2][N:7]1[CH2:8][CH2:9][S:10][C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190791794-(2-(2-Hydroxymethylbenzoyl)aminoethylthio]pyridine

Product 1

HCID 569828894-(2-(Isoindolin-1-on-2-yl)ethylthio]pyridineYield 57.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.153 g (4.0 mmol) of 4-[2-(2-hydroxymethylbenzoyl)aminoethylthio]pyridine and 1.68 ml (12.1 mmol) of triethylamine in 50 ml of methylene chloride, 0.62 ml (8.0 mmol) of methanesulfonyl chloride was added with stirring at room temperature, and the mixture was stirred at room temperature for 30 minutes. The mixture was washed with saturated aqueous sodium bicarbonate, water and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 623 mg of the desired compound (57.6% yield, colorless crystals), mp. 86°-87° C.

Workup

  1. stirringthe mixture was stirred at room temperature for 30 minutes
  2. washThe mixture was washed with saturated aqueous sodium bicarbonate, water and saturated saline
  3. dry with materialdried over anhydrous magnesium sulfate
  4. distillationThe solvent was distilled off
  5. customthe residue was purified by column chromatography (eluent: ethyl acetate)

Sources & evidence

ORD record
ord-a5cf6e169638414f92985c34a5a2a735
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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