Ethyl Bromide → N-Ethyl-N-methyl-2-thiophene methanamine

HRID 1732894

Reaction equation

HRID 1732894 reaction equation
BrCC.[CH2:4]([N:6]([CH2:9][CH3:10])[CH2:7][CH3:8])C.CNC[C:14]1[S:15]C=[CH:17][CH:18]=1>C1(C)C=CC=CC=1.O.C(=O)(O)[O-].[Na+]>[CH2:7]([N:6]([CH3:4])[CH2:9][C:10]1[S:15][CH:14]=[CH:18][CH:17]=1)[CH3:8]

Participants

7

Reactant 3

HCID 6332Ethyl BromideHCID 8471TriethylamineHCID 436153N-Methyl-1-(thiophen-2-yl)methanamine

Product 1

HCID 12788071N-Ethyl-N-methyl-2-thiophene methanamine

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1140TolueneSolventHCID 516892Sodium BicarbonateSolvent

Procedure

Bromoethane (150 ml), triethylamine (7.3 ml) and N-methyl-2-thiophenemethanamine (21.2 g) were stirred at room temperature in toluene (212 ml) for 4 days. The solution was diluted with water, saturated with sodium bicarbonate and extracted with ethyl acetate. The organic extracts were distilled to give the title compound as an oil (13.6 g) b.p. 46° (16 mm).

Workup

  1. extractionextracted with ethyl acetate
  2. distillationThe organic extracts were distilled

Sources & evidence

ORD record
ord-2cc545f257c747f1846a3e4260f3340f
Source dataset
uspto-grants-1980_12
Patent number
US04239769

Linked notes

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