Dimethylformamide → N-benzyl-2-formyl-4-methylthiazole-5-carboxamide

HRID 2381799Notes

Reaction equation

HRID 2381799 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][CH:14]=[N:13][C:12]=1[CH3:16])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C[Si]([N-][Si](C)(C)C)(C)C.[Li+].CN(C)[CH:29]=[O:30]>O1CCCC1>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([CH:29]=[O:30])=[N:13][C:12]=1[CH3:16])=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 2733832Lithium HexamethyldisilazideHCID 45823040HCID 45823040, compound

Product 1

HCID 73213265N-benzyl-2-formyl-4-methylthiazole-5-carboxamideYield 98%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of N-benzyl-4-methylthiazole-5-carboxamide (1.00 g, 4.31 mmol) in tetrahydrofuran (20 mL) was added lithium bis(trimethylsilyl)amide (9.5 mL of 1.0 M solution in tetrahydrofuran, 9.5 mmol) at −78° C. The reaction mixture was stirred for 5 minutes, and N,N-dimethylformamide (0.35 mL, 4.54 mmol) was added. The reaction mixture was slowly warmed to ambient temperature over 4 hours, quenched with 5% hydrochloric acid (10 mL), extracted with ethyl acetate. The organic layer was washed with water and brine, dried over anhydrous sodium sulfate, filtered, and concentrated in vacuo. The residue was purified by column chromatography to afford the title compound in 98% yield (1.1 g): MS (ES+) m/z 261.1 (M+1).

Workup

  1. customquenched with 5% hydrochloric acid (10 mL)
  2. extractionextracted with ethyl acetate
  3. washThe organic layer was washed with water and brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-0b04be7b69104f34bc471c1727a0d450
Source dataset
uspto-grants-2012_09
Patent number
US08258160B2

Reaction notes

Loading…