2-(Methylamino)ethanol → HCID 67218500, compound

HRID 900890Notes

Reaction equation

HRID 900890 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].[O-2].[Mg+2].[Cl:8][C:9]1[S:13][C:12]([S:14](Cl)(=[O:16])=[O:15])=[CH:11][C:10]=1[N+:18]([O-:20])=[O:19]>C1COCC1.O>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[S:14]([C:12]1[S:13][C:9]([Cl:8])=[C:10]([N+:18]([O-:20])=[O:19])[CH:11]=1)(=[O:16])=[O:15]

Participants

6

Reactant 3

HCID 80162-(Methylamino)ethanolHCID 27357835-Chloro-4-nitrothiophene-2-sulfonyl chlorideHCID 6850729Magnesium monoxide

Product 1

HCID 67218500HCID 67218500, compoundYield 35%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A suspension of 2-(methylamino)-ethanol (0.29 g, 3.86 mmol) and magnesium oxide (0.77 g, 19.1 mmol) in THF (4 ml) and water (1.4 ml) was allowed to stir at room temperature for 30 min, 5-chloro-4-nitrothiophene-2-sulfonyl chloride (1.0 g, 3.81 mmol) dissolved in THF (1.6 ml) was added drop wise at room temperature over a period of 1 h and the reaction mixture was allowed to stir for an additional hour. Filtration over Decalite and evaporation yielded the crude product which was further purified by flash chromatography on silica gel (ethyl acetate/heptane) to yield 5-chloro-4-nitro-thiophene-2-sulfonic acid (2-hydroxy-ethyl)-methyl-amide (0.4 g, 35%) as a yellow solid. MS (EI) 300.0 [(M)+], mp 62° C.

Workup

  1. additionwas added drop wise at room temperature over a period of 1 h
  2. stirringto stir for an additional hour
  3. filtrationFiltration
  4. customover Decalite and evaporation
  5. customyielded the crude product which
  6. customwas further purified by flash chromatography on silica gel (ethyl acetate/heptane)

Sources & evidence

ORD record
ord-06350309ea39494daddb8c3cc55df3b3
Source dataset
uspto-grants-2008_04
Patent number
US07361659B2

Reaction notes

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