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

HRID 2210166Notes

Reaction equation

HRID 2210166 reaction equation
O[CH2:2][C:3]1[CH:22]=[CH:21][CH:20]=[CH:19][C:4]=1[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=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:22][CH:21]=[CH:20][CH:19]=2)[CH2:2][N:7]1[CH2:8][CH2:9][CH2:10][CH2:11][S:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190791544-[4-(2-Hydroxymethylbenzoyl)aminobutylthio]pyridine

Product 1

HCID 190790754-[4-(Isoindolin-1-on-2-yl)butylthio]pyridineYield 72.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.58 g (5.0 mmol) of 4-[4-(2-hydroxymethylbenzoyl)aminobutylthio]pyridine and 2.09 ml (15.0 mmol) of triethylamine in 50 ml of methylene chloride, 0.77 ml (10.0 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 1.075 g of the desired compound (72.1% yield, pale brown crystals), mp. 57°-58° 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-af6a952648e240a09ec6b4edc5b2d159
Source dataset
uspto-grants-1995_10
Patent number
US05457106

Reaction notes

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