Tetrahydrofuran → 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

HRID 559506Notes

Reaction equation

HRID 559506 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)#N.CC(C[AlH]CC(C)C)C.C1C[O:33]CC1>>[CH:1]([C:3]1[CH:8]=[CH:7][C:6]([S:9]([N:12]([CH2:18][O:19][CH3:20])[C:13]2[S:14][CH:15]=[CH:16][N:17]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1)=[O:33]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14487Diisobutylaluminum hydrideHCID 670014474-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Product 1

HCID 866116984-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide

Procedure

To a solution of 4-cyano-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (4.5 mmol) in THF (50 mL) at −78° C. under argon was added DIBAL (5.0 mmol, 1M in THF) and the solution was allowed to warm to room temperature overnight. After the reaction was quenched with potassium sodium tartrate solution slowly, the mixture was extracted with ethyl acetate, and the organic phase was washed with brine, dried over MgSO4, and concentrated in vacuo. The crude product was purified by column chromatography to give 4-formyl-N-methoxymethyl-N-thiazol-2-yl-benzenesulfonamide (3.1 mmol).

Workup

  1. customAfter the reaction was quenched with potassium sodium tartrate solution slowly
  2. extractionthe mixture was extracted with ethyl acetate
  3. washthe organic phase was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-13bb3891a3c84102971122be65d9405f
Source dataset
uspto-grants-2011_11
Patent number
US08063080B2

Reaction notes

Loading…