2-Methoxyethylamine → HCID 20292409, compound

HRID 1413537Notes

Reaction equation

HRID 1413537 reaction equation
[CH3:1][O:2][CH2:3][CH2:4][NH2:5].Cl[C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[S:16]([O-:19])(=[O:18])=[O:17].[Na+:20]>[Cl-].[Na+]>[CH3:1][O:2][CH2:3][CH2:4][NH:5][C:7]1[CH:12]=[CH:11][C:10]([N+:13]([O-:15])=[O:14])=[CH:9][C:8]=1[S:16]([O-:19])(=[O:18])=[O:17].[Na+:20]

Participants

4

Reactant 2

HCID 80182-MethoxyethylamineHCID 70350Benzenesulfonic acid, 2-chloro-5-nitro-, sodium salt (1:1)

Product 1

HCID 20292409HCID 20292409, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 5234Sodium ChlorideSolvent

Procedure

To 30 ml of 2-methoxyethylamine, 27.5 g (0.1 mol) of sodium 2-chloro-5-nitrobenzenesulfonate was added. The reaction mixture was heated on a steam bath with stirring for 1 hour. After cooling, 100 ml of a saturated aqueous sodium chloride solution was added to the mixture. The crystals thus-precipitated were collected by filtration and washed with acetone to obtain about 30 g (yield: 87%) of sodium 2-(2-methoxyethylamino)-5-nitrobenzenesulfonate. This compound (30 g) was suspended in 100 ml of dimethylformamide. To the mixture anhydrous potassium carbonate (20 g) and methoxyethyl bromide (21g) were added, and heated on a steam bath with stirring for 1 hour. The reaction mixture was added to 100 ml of water and the insoluble materials were removed by filtration. To the filtrate an aqueous hydrochloric acid was added to render an acid condition. The crystals thus-precipitated were collected by filtration to obtain about 21 g (yield: 60%) of sodium 2-bis(2-methoxyethyl)amino-5-nitrobenzensulfonate. Melting Point: 202°-204° C.

Workup

  1. temperatureThe reaction mixture was heated on a steam bath
  2. temperatureAfter cooling
  3. customThe crystals thus-precipitated
  4. filtrationwere collected by filtration
  5. washwashed with acetone

Sources & evidence

ORD record
ord-6a958719f86a421cb3802aa933979056
Source dataset
uspto-grants-1981_02
Patent number
US04250246

Reaction notes

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