Sodium Hydroxide → HCID 54931697, compound

HRID 1157587Notes

Reaction equation

HRID 1157587 reaction equation
Cl.[N+:2]([C:5]1[CH:6]=[C:7]([CH:10]=[CH:11][CH:12]=1)[CH2:8][NH2:9])([O-:4])=[O:3].[OH-].[Na+].[CH3:15][S:16]([CH:19]=[CH2:20])(=[O:18])=[O:17]>C(Cl)Cl>[CH3:15][S:16]([CH2:19][CH2:20][NH:9][CH2:8][C:7]1[CH:10]=[CH:11][CH:12]=[C:5]([N+:2]([O-:4])=[O:3])[CH:6]=1)(=[O:18])=[O:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 19354Methyl vinyl sulfoneHCID 2724030Benzenemethanamine, 3-nitro-, hydrochloride (1:1)

Product 1

HCID 54931697HCID 54931697, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 3-nitrobenzylamine hydrochloride (1.0 g, 5.3 mmol) in DCM was converted to the free base by treating with 2 N NaOH. The organic layer was separated and concentrated, and the residue was redissolved in MeOH. To this solution was added methylvinylsulfone (232 μL, 2.6 mmol), and the reaction was stirred at rt. After 5 h, the crude reaction mixture was adsorbed onto silica gel and purified by column chromatography to generate the title compound in quantitative yield. 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 8.13 (d, J=8.2 Hz, 1H), 7.67 (d, J=7.5 Hz, 1H), 7.51 (t, J=7.9 Hz, 1H), 3.93 (s, 2H), 3.16-3.24 (m, 4H), 3.01 (s, 3H). ES-LC/MS m/z=259 [M+H]+.

Workup

  1. customThe organic layer was separated
  2. concentrationconcentrated
  3. dissolutionthe residue was redissolved in MeOH
  4. customthe crude reaction mixture
  5. custompurified by column chromatography

Sources & evidence

ORD record
ord-13157effd0bb496abe651a7c929cd247
Source dataset
uspto-grants-2010_10
Patent number
US07807673B2

Reaction notes

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