Sodium borohydride → HCID 21280987, compound

HRID 414511Notes

Reaction equation

HRID 414511 reaction equation
[CH3:1][O:2][C:3]1[CH:13]=[C:12]([C:14](=[O:20])[CH2:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:11]=[C:10]([O:21][CH3:22])[C:4]=1[N:5]([CH3:9])[C:6](=[O:8])[CH3:7].[BH4-].[Na+]>C(O)C>[OH:20][CH:14]([C:12]1[CH:13]=[C:3]([O:2][CH3:1])[C:4]([N:5]([CH3:9])[C:6](=[O:8])[CH3:7])=[C:10]([O:21][CH3:22])[CH:11]=1)[CH2:15][S:16]([CH3:19])(=[O:17])=[O:18]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21280953HCID 21280953, compound

Product 1

HCID 21280987HCID 21280987, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 20.9 g. of 2',6'-dimethoxy-N-methyl-4'-[(methylsulfonyl)acetyl]-acetanilide and 9.5 g. of sodium borohydride in 300 ml. of ethanol was stirred at room temperature for 20 hours. The solution was diluted with 300 ml. of water and the alcohol removed under vacuum. The resulting suspension was extracted with two 1 liter portions of ethyl acetate. The ethyl acetate extracts were washed with two 200 ml. portions of water, combined, dried over magnesium sulfate and evaporated under vacuum. Recrystallization of the residue from ethyl acetate gave 4'-[1-hydroxy-2-(methylsulfonyl)-ethyl]-2',6'-dimethoxy-N-methylacetanilide having a melting point of 175°-177° C.

Workup

  1. additionA suspension of 20.9 g
  2. additionThe solution was diluted with 300 ml
  3. customof water and the alcohol removed under vacuum
  4. extractionThe resulting suspension was extracted with two 1 liter portions of ethyl acetate
  5. washThe ethyl acetate extracts were washed with two 200 ml
  6. dry with materialdried over magnesium sulfate
  7. customevaporated under vacuum
  8. customRecrystallization of the residue from ethyl acetate

Sources & evidence

ORD record
ord-a9f6bc27f1894d6195efbf42924cb5fe
Source dataset
uspto-grants-1988_12
Patent number
US04792557

Reaction notes

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