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

HRID 661062Notes

Reaction equation

HRID 661062 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-0f29591527ac4288b756e5080bee05f2
Source dataset
uspto-grants-2011_12
Patent number
US08084479B2

Reaction notes

Loading…