Ethylenediamine → HCID 18476172, compound

HRID 2187652Notes

Reaction equation

HRID 2187652 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11](OCC)=O)[S:7][C:6]=2[CH:16]=1.[CH2:17]([NH2:20])[CH2:18][NH2:19].[Si](I)(C)(C)C>C(N(CC)CC)C>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([Cl:10])=[C:8]([C:11]3[NH:19][CH2:18][CH2:17][N:20]=3)[S:7][C:6]=2[CH:16]=1

Participants

5

Reactant 3

HCID 3301EthylenediamineHCID 85247Trimethylsilyl iodideHCID 4089267HCID 4089267, compound

Product 1

HCID 18476172HCID 18476172, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 4 g (12.5 mmol) ethyl 6-bromo-3-chlorobenzo[b]thiophen-2-carboxylate and 7.5 g (125 mmol) ethylendiamine were heated at 80° C. overnight. It was concentrated in vacuo, and the crude 2-ethylaminoamide was dissolved in 70 ml dry dichloromethane followed by addition of 10.5 ml triethylamine and 15 g (75 mmol) TMS iodide. After five days stirring at room temperature the reaction was almost complete as detected by TLC. It was extracted with water, dried over sodium sulfate, and concentrated under reduced pressure. The title imidazoline was isolated from the residue by column chromatography on silica gel with dichloromethane/ethanolic ammonia gradient.

Workup

  1. concentrationIt was concentrated in vacuo
  2. dissolutionthe crude 2-ethylaminoamide was dissolved in 70 ml dry dichloromethane
  3. extractionIt was extracted with water
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c5b5b331f00343418fd1666840294afb
Source dataset
uspto-grants-2002_06
Patent number
US06410562B1

Reaction notes

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