Dimethylamine → N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamide

HRID 2109735Notes

Reaction equation

HRID 2109735 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1.[CH3:12][NH:13][CH3:14]>C1COCC1>[CH3:12][N:13]([CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1)[CH3:14]

Participants

4

Reactant 2

HCID 674DimethylamineHCID 819632-Acetamido-4-chloromethylthiazole

Product 1

HCID 57634222N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamideYield 80%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-(4-(Chloromethyl)thiazol-2-yl)acetamide (2.0 g, 10 mmol) in 20 mL THF was added in portions to dimethylamine (4.7 g, 105 mmol). After addition, the mixture was stirred for an additional 30 minutes. The solvent was removed under reduced pressure. 200 mL distilled water was then added to the resulting residue, and the mixture was extracted with EtOAc. The EtOAc solution was washed with brine solution and dried over sodium sulfate. After removing the solvent, an off-white solid was obtained as the crude product (1.3 g, yield=80%). LCMS (API-ES) m/z (%) 200.1 (100%, M++H). 1H NMR (400 MHz, CDCl3) δ ppm 2.24 (s, 3H) 2.26 (s, 6H) 3.43 (s, 2H) 6.73 (s, 1H).

Workup

  1. additionAfter addition
  2. customThe solvent was removed under reduced pressure
  3. distillation200 mL distilled water
  4. additionwas then added to the resulting residue
  5. extractionthe mixture was extracted with EtOAc
  6. washThe EtOAc solution was washed with brine solution
  7. dry with materialdried over sodium sulfate
  8. customAfter removing the solvent

Sources & evidence

ORD record
ord-b01963d22d2e4c539c0571cedb6f8680
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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