Triethylamine → HCID 67219807, compound

HRID 900880Notes

Reaction equation

HRID 900880 reaction equation
[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH2:5].[Cl:7][C:8]1[S:12][C:11]([S:13](Cl)(=[O:15])=[O:14])=[CH:10][C:9]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C>O1CCOCC1>[CH3:1][N:2]([CH3:6])[CH2:3][CH2:4][NH:5][S:13]([C:11]1[S:12][C:8]([Cl:7])=[C:9]([N+:17]([O-:19])=[O:18])[CH:10]=1)(=[O:15])=[O:14]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 66053N,N-DimethylethylenediamineHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chloride

Product 1

HCID 67219807HCID 67219807, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a stirred solution of N,N-dimethylethylenediamine (0.67 g, 7.6 mmol) in dioxane (25 ml) was added at room temperature 5-chloro-4-nitrothiophene-2-sulfonyl chloride (2.0 g, 7.64 mmol) and triethylamine (1.17 ml, 8.4 mmol). The light yellow suspension was stirred at room temperature for 17 h, and evaporated. The crude product was further purified by flash chromatography on silica gel (dichloromethane/methanol), and subsequent crystallization from ethyl acetate to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-dimethylamino-ethyl)-amide (1.16 g, 48%) as a light brown solid. MS (ISP) 312.0 [(M−H)−], mp 178° C.

Workup

  1. customevaporated
  2. customThe crude product was further purified by flash chromatography on silica gel (dichloromethane/methanol), and subsequent crystallization from ethyl acetate

Sources & evidence

ORD record
ord-d2962c7c4b42451f9d8a598e2f52bd59
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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