Triethylamine → HCID 57089298, compound

HRID 6159Notes

Reaction equation

HRID 6159 reaction equation
O[CH2:2][C:3]1[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=1[C:5]([NH:7][CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=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:21][CH:20]=[CH:19][CH:18]=2)[CH2:2][N:7]1[CH2:8][CH2:9][CH2:10][S:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 190791424-[3-(2-Hydroxymethylbenzoyl)aminopropylthio]pyridine

Product 1

HCID 57089298HCID 57089298, compoundYield 78.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1.51 g (5.0 mmol) of 4-[3-(2-hydroxymethylbenzoyl)aminopropylthio]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 1.12 g of the desired compound (78.9% yield, pale brown crystals), mp. 73°-74.5° 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-0be3a0bcf2234748992476eebd2f65be
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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