Sodium borohydride → 4-[4-(2-Hydroxymethylbenzoyl)aminobutylthio]pyridine

HRID 274697Notes

Reaction equation

HRID 274697 reaction equation
[C:1]1(=[O:22])[N:5]([CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=2)[C:4](=[O:17])[C:3]2=[CH:18][CH:19]=[CH:20][CH:21]=[C:2]12.[BH4-].[Na+]>C(O)C>[OH:22][CH2:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[C:4]([NH:5][CH2:6][CH2:7][CH2:8][CH2:9][S:10][C:11]1[CH:12]=[CH:13][N:14]=[CH:15][CH:16]=1)=[O:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 14538888HCID 14538888, compound

Product 1

HCID 190791544-[4-(2-Hydroxymethylbenzoyl)aminobutylthio]pyridineYield 73.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 6.25 g of (20.0 mmol) of 4-(4-phthalimidobutylthio)pyridine in 300 ml of ethanol, 7.57 g (200 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 14 hours. The solvent was distilled off and saturated saline was added to the residue. The mixture was extracted with chloroform and the extract was dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10) to give 4.63 g of the desired compound (73.1% yield, colorless crystals), mp. 87°-88° C.

Workup

  1. distillationThe solvent was distilled off
  2. additionsaturated saline was added to the residue
  3. extractionThe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. distillationThe solvent was distilled off
  6. customthe residue was purified by column chromatography (eluent: ethanol/ethyl acetate=1:10)

Sources & evidence

ORD record
ord-050722690b8244edb11cb2b362dfa77f
Source dataset
uspto-grants-1995_02
Patent number
US05389658

Reaction notes

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