Sodium borohydride → 4-(2-(2-Hydroxymethylbenzoyl)aminoethylthio]pyridine

HRID 6151Notes

Reaction equation

HRID 6151 reaction equation
[C:1]1(=[O:20])[N:5]([CH2:6][CH2:7][S:8][C:9]2[CH:14]=[CH:13][N:12]=[CH:11][CH:10]=2)[C:4](=[O:15])[C:3]2=[CH:16][CH:17]=[CH:18][CH:19]=[C:2]12.[BH4-].[Na+].C(O)C.C(OCC)(=O)C>C(O)C>[OH:20][CH2:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:5][CH2:6][CH2:7][S:8][C:9]1[CH:10]=[CH:11][N:12]=[CH:13][CH:14]=1)=[O:15]

Participants

5

Reactant 3

HCID 4311764Sodium borohydrideHCID 190792564-(2-Phthalimidoethylthio)pyridineHCID 21584252Ethanol ethylacetate

Product 1

HCID 190791794-(2-(2-Hydroxymethylbenzoyl)aminoethylthio]pyridineYield 77.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2.84 g (10.0 mmol) of 4-(2-phthalimidoethylthio)pyridine in 150 ml of ethanol, 3.78 g (100 mmol) of sodium borohydride was added, and the mixture was stirred at room temperature for 3 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 2.24 g of the desired compound (77.8% yield, colorless crystals), mp. 132°-133° 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

Sources & evidence

ORD record
ord-b2748f3faf0e4cadb94edae14f08f39f
Source dataset
uspto-grants-1993_09
Patent number
US05246948

Reaction notes

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