2,2-Diethoxyethylamine → N-(2,2-diethoxyethyl)-N-[(2-methyl-1,3-thiazol-4-yl)methyl]amine

HRID 216289Notes

Reaction equation

HRID 216289 reaction equation
Cl[CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1.[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][NH2:14])[CH3:10]>O1CCCC1>[CH2:9]([O:11][CH:12]([O:15][CH2:16][CH3:17])[CH2:13][NH:14][CH2:2][C:3]1[N:4]=[C:5]([CH3:8])[S:6][CH:7]=1)[CH3:10]

Participants

4

Reactant 2

HCID 695242,2-DiethoxyethylamineHCID 7363414-(Chloromethyl)-2-methyl-1,3-thiazole

Product 1

HCID 66890752N-(2,2-diethoxyethyl)-N-[(2-methyl-1,3-thiazol-4-yl)methyl]amineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-Chloromethyl-2-methylthiazole (0.6 g, 4 mmol) was added to aminoacetaldehyde diethyl acetal (5 mL, 10 equivalents) dissolved in tetrahydrofuran (15 mL) at 25° C., and the mixture was stirred for 16 h. The solvents were evaporated and the excess aldehyde was distilled from the crude mixture. The crude residue was purified using dichloromethane—dichloromethane/10% methanol to give 0.76 g (76%) of the title compound.

Workup

  1. customThe solvents were evaporated
  2. distillationthe excess aldehyde was distilled from the crude mixture
  3. customThe crude residue was purified

Sources & evidence

ORD record
ord-ab07e9a956ff4e5093f9fb13fc898232
Source dataset
uspto-grants-2012_06
Patent number
US08193227B2

Reaction notes

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