Dichloromethane → Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylate

HRID 872671Notes

Reaction equation

HRID 872671 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([CH2:11]Cl)[S:9][CH:10]=1)=[O:5])[CH3:2].C(=O)([O-])[O-].[K+].[K+].Cl.[CH3:20][NH:21][CH3:22].C(Cl)Cl>CN(C=O)C>[CH3:20][N:21]([CH2:11][C:8]1[S:9][CH:10]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:7]=1)[CH3:22]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 10473Dimethylamine, hydrochlorideHCID 11430Potassium CarbonateHCID 24715135Ethyl 2-(chloromethyl)-1,3-thiazole-4-carboxylate

Product 1

HCID 2039211Ethyl 2-((dimethylamino)methyl)thiazole-4-carboxylateYield 34.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

2-Chloromethyl-thiazole-4-carboxylic acid ethyl ester (500 mg, 2.431 mmol) and potassium carbonate (504 mg, 3.65 mmol) were dissolved in dry DMF. Dimethylamine hydrochloride (218 mg, 2.67 mmol) in dry DMF was added slowly to the reaction mixture and stirred at RT over three nights. DCM was added and the mixture was washed with concentrated NaHCO3 and water. Organic phase was evaporated to dryness and the product was purified by Flash-chromatography. Yield 34.2%. 1H-NMR (400 MHz; CDCl3): δ 1.41 (t, 3H), 2.49 (s, 6H), 3.99 (s, 2H) 4.43 (q, 2H), 8.20 (s, 1H).

Workup

  1. washthe mixture was washed with concentrated NaHCO3 and water
  2. customOrganic phase was evaporated to dryness
  3. customthe product was purified by Flash-chromatography

Sources & evidence

ORD record
ord-24a52f0a45694d8e954b1aa47589d923
Source dataset
uspto-grants-2015_03
Patent number
US08975254B2

Reaction notes

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