Dimethylformamide → HCID 59742743, compound

HRID 1946960Notes

Reaction equation

HRID 1946960 reaction equation
[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[CH:9][N:8]=[C:7]1[Si:11]([C:14]([CH3:17])([CH3:16])[CH3:15])([CH3:13])[CH3:12])(=[O:5])=[O:4].C([Li])CCC.CN([CH:27]=[O:28])C>C1COCC1>[CH3:1][N:2]([CH3:18])[S:3]([N:6]1[CH:10]=[C:9]([CH:27]=[O:28])[N:8]=[C:7]1[Si:11]([C:14]([CH3:15])([CH3:17])[CH3:16])([CH3:13])[CH3:12])(=[O:4])=[O:5]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 64202092-(tert-Butyldimethylsilyl)-N,N-dimethyl-1H-imidazole-1-sulfonamideHCID 178418339Butyllithium

Product 1

HCID 59742743HCID 59742743, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred, cooled (−78° C.) solution of 2-(tert-butyl-dimethyl-silanyl)-imidazole-1-sulfonic acid dimethylamide (1.02 g; CAS 129378-52-5) in THF (20 ml) under an argon atmosphere was added dropwise butyl lithium (3.3 ml; 1.6 M solution in hexanes) over a period of 10 minutes. After 30 minutes of stirring, DMF (1.3 ml) was added over a period of 5 minutes and the mixture (clear light yellow solution) was stirred at −78° C. for another 2 hours. The mixture was quenched with saturated aqueous NH4Cl and diluted with EtOAc. The aqueous phase was back extracted with EtOAc. The combined organics were washed with H2O and brine, dried over MgSO4, filtered and concentrated to give 2-(tert-butyl-dimethyl-silanyl)-4-formyl-imidazole-1-sulfonic acid dimethylamide (1.22 g) as viscous orange oil which was used in the next reaction step without further purification. MS (ISP): 318.3 ([M+H]+)

Workup

  1. stirringthe mixture (clear light yellow solution) was stirred at −78° C. for another 2 hours
  2. customThe mixture was quenched with saturated aqueous NH4Cl
  3. additiondiluted with EtOAc
  4. extractionThe aqueous phase was back extracted with EtOAc
  5. washThe combined organics were washed with H2O and brine
  6. dry with materialdried over MgSO4
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-202a425e3fbf498b8a92a6935b7134f8
Source dataset
uspto-grants-2013_03
Patent number
US08399463B2

Reaction notes

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