2-(Methylamino)ethanol → HCID 13881286, compound

HRID 1906906Notes

Reaction equation

HRID 1906906 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][OH:5].Cl[S:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:9])=[O:8]>C1COCC1>[OH:5][CH2:4][CH2:3][N:2]([CH3:1])[S:7]([C:10]1[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[C:11]=1[C:12]([O:14][CH3:15])=[O:13])(=[O:8])=[O:9]

Participants

4

Reactant 2

HCID 80162-(Methylamino)ethanolHCID 13670189Methyl 2-(chlorosulfonyl)-6-nitrobenzoate

Product 1

HCID 13881286HCID 13881286, compoundYield 82.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

N-Methylethanolamine (2.96 g, 39.4 mmol) was added to a solution of methyl 2-chlorosulfonyl-6nitrobenzoate (5.5 g, 19.7 mmol) in THF (150 ml) and the mixture stirred at 20°-25° for 18 hours. After removing THF under reduced pressure, the residue was partitioned between EtOAc and H2O. The organic extract was washed with saturated NaCl solution and dried (Na2SO4). Flash chromatography of the residue over silica gel and elution with 1% MeOH-99% CHCl3 afforded pure sulfonamide. Recrystallization from EtOAc-hexane gave analytically pure product (5.2 g, 82.9%), m.p. 98°-101°.

Workup

  1. customAfter removing THF under reduced pressure
  2. customthe residue was partitioned between EtOAc and H2O
  3. extractionThe organic extract
  4. washwas washed with saturated NaCl solution
  5. dry with materialdried (Na2SO4)
  6. washFlash chromatography of the residue over silica gel and elution with 1% MeOH-99% CHCl3 afforded pure sulfonamide
  7. customRecrystallization from EtOAc-hexane

Sources & evidence

ORD record
ord-5d69e36c625c49c08a64cdd88838f670
Source dataset
uspto-grants-1987_03
Patent number
US04654369

Reaction notes

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