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

HRID 418345Notes

Reaction equation

HRID 418345 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.C([O-])([O-])=O.[Na+].[Na+].[CH3:18][NH:19][CH3:20]>C1COCC1>[CH3:18][N:19]([CH2:2][C:3]1[N:4]=[C:5]([NH:8][C:9](=[O:11])[CH3:10])[S:6][CH:7]=1)[CH3:20]

Participants

5

Reactant 3

HCID 674DimethylamineHCID 10340Sodium CarbonateHCID 819632-Acetamido-4-chloromethylthiazole

Product 1

HCID 57634222N-[4-[(Dimethylamino)methyl]-2-thiazolyl]acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

Dissolved N-(4-chloromethyl-thiazol-2-yl)-acetamide (250 mg, 1.31 mmol) in 5 mL of THF. To this was added Na2CO3 (250 mg). Bubbled dimethyl amine in for 15 min. Sealed the flask and heated at 50° C. for 2 h. LC-MS analysis indicated the desired adduct. Filtered the mixture through diatomaceous earth and washed plug with 2×10 mL of THF. Concentrated to dryness to give 274 mg of N-(4-dimethylaminomethyl-thiazol-2-yl)-acetamide.

Workup

  1. customin for 15 min
  2. customSealed the flask
  3. filtrationFiltered the mixture through diatomaceous earth
  4. washwashed plug with 2×10 mL of THF
  5. concentrationConcentrated to dryness

Sources & evidence

ORD record
ord-f7d49d438ca14202acabd2406b850de1
Source dataset
uspto-grants-2012_01
Patent number
US08093266B2

Reaction notes

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