Formaldehyde → 5-dimethylamino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1164295Notes

Reaction equation

HRID 1164295 reaction equation
N[C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([S:8]([NH:11][C:12]([NH:14][C:15]2[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=2)=[O:13])(=[O:10])=[O:9])[CH:7]=1.[C:25]([BH3-])#[N:26].[Na+].[CH2:29]=O.[OH-].[Na+]>C(#N)C.O.C(O)(=O)C>[CH3:29][N:26]([CH3:25])[C:2]1[CH:3]=[CH:4][C:5]([Cl:24])=[C:6]([S:8]([NH:11][C:12]([NH:14][C:15]2[N:20]=[C:19]([O:21][CH3:22])[N:18]=[C:17]([CH3:23])[N:16]=2)=[O:13])(=[O:10])=[O:9])[CH:7]=1

Participants

8

Reactant 4

HCID 712FormaldehydeHCID 14798Sodium HydroxideHCID 5003444Sodium cyanoborohydrideHCID 20455856HCID 20455856, compound

Product 1

HCID 204558515-dimethylamino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolvent2×HCID 962WaterSolventHCID 6342AcetonitrileSolvent

Procedure

To an agitated solution of 3.7 g of 5-amino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide and 0.88 g of sodium cyanoborohydride in 50 ml of acetonitrile is added 3 ml of formalin. To the reaction mixture is then added 1 ml of glacial acetic acid over a period of 10 minutes. The reaction is then stirred at room temperature for 2 hours, another ml of glacial acetic acid is added and stirring is continued for an additional 30 minutes. The reaction mixture is then poured into 50 ml of water, brought to pH 7 by the addition of aqueous sodium hydroxide and extracted several times with methylene chloride. The combined methylene chloride extracts are washed with brine and dried over anhydrous magnesium sulfate. Evaporation of the solvent in vacuo yields the desired product, 5-dimethylamino-2-chloro-N-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)aminocarbonyl]benzenesulfonamide.

Workup

  1. stirringstirring
  2. waitis continued for an additional 30 minutes
  3. extractionextracted several times with methylene chloride
  4. washThe combined methylene chloride extracts are washed with brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customEvaporation of the solvent in vacuo

Sources & evidence

ORD record
ord-b5251c3d512f4265820a5abb3b052b62
Source dataset
uspto-grants-1983_01
Patent number
US04369058

Reaction notes

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