Sodium Formaldehyde Bisulfite → sodium N-(3-carbamoylphenyl)-N-(2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)aminomethanesulfonate dihydrate

HRID 704126Notes

Reaction equation

HRID 704126 reaction equation
O.O.O.[C:4]([C:7]1[CH:8]=[C:9]([NH:13][CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[O:16])[CH:10]=[CH:11][CH:12]=1)(=[O:6])[NH2:5].[OH:30][CH2:31][S:32]([O-:35])(=[O:34])=[O:33].[Na+:36]>O>[OH2:6].[OH2:30].[C:4]([C:7]1[CH:8]=[C:9]([N:13]([CH2:31][S:32]([O-:35])(=[O:34])=[O:33])[CH2:14][C:15]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)=[O:16])[CH:10]=[CH:11][CH:12]=1)(=[O:6])[NH2:5].[Na+:36]

Participants

4

Reactant 2

HCID 2723822Sodium Formaldehyde BisulfiteHCID 221497912-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide trihydrate

Product 1

HCID 86744520sodium N-(3-carbamoylphenyl)-N-(2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)aminomethanesulfonate dihydrateYield 47.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

200 g of 2-(3-carbamoylphenylamino)-N-(3,4-dimethoxyphenethyl)acetamide trihydrate and 65.2 g of sodium hydroxymethanesulfonate were suspended in 400 ml of water, and the suspension was refluxed over night. After cooling, the reaction mixture was washed with chloroform, and an insoluble material was removed by filtration. The filtrate was concentrated in vacuo. The residue was dissolved in a mixture of 500 ml of water and 500 ml of ethanol under heating, and then the solution was cooled. The precipitate formed was collected by filtration and recrystallized from a mixture of water and ethanol to give 59.2 g of sodium N-(3-carbamoylphenyl)-N-(2-((2-(3,4-dimethoxyphenyl)ethyl)amino)-2-oxoethyl)aminomethanesulfonate dihydrate as colorless crystals with m.p. 253° to 255° C. (decomposition).

Workup

  1. temperaturethe suspension was refluxed over night
  2. temperatureAfter cooling
  3. washthe reaction mixture was washed with chloroform
  4. customan insoluble material was removed by filtration
  5. concentrationThe filtrate was concentrated in vacuo
  6. dissolutionThe residue was dissolved in a mixture of 500 ml of water and 500 ml of ethanol
  7. temperatureunder heating
  8. temperaturethe solution was cooled
  9. customThe precipitate formed
  10. filtrationwas collected by filtration
  11. customrecrystallized from a mixture of water and ethanol

Sources & evidence

ORD record
ord-b91cade261054fdc9ee2684d8d90b054
Source dataset
uspto-grants-1991_01
Patent number
US04985595

Reaction notes

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