Sodium → 2-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

HRID 1164293Notes

Reaction equation

HRID 1164293 reaction equation
[Na].[CH3:2][O:3][C:4]1[CH:9]=[C:8]([CH3:10])[N:7]=[C:6]([NH:11][C:12]([NH:14][S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][C:19]=2[N+:24]([O-])=O)(=[O:17])=[O:16])=[O:13])[N:5]=1.[H][H]>[Pd].C(O)(=O)C>[NH2:24][C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[S:15]([NH:14][C:12]([NH:11][C:6]1[N:5]=[C:4]([O:3][CH3:2])[CH:9]=[C:8]([CH3:10])[N:7]=1)=[O:13])(=[O:17])=[O:16]

Participants

6

Reactant 3

HCID 5360545SodiumHCID 14774713N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamideHCID 178418361HCID 178418361, compound

Product 1

HCID 131382142-Amino-N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]benzenesulfonamide

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 176Acetic AcidSolvent

Procedure

A suspension containing 2 g of the sodium salt of N-[(4-methoxy-6-methylpyrimidin-2-yl)aminocarbonyl]-2-nitrobenzenesulfonamide, 25 ml of glacial acetic acid and 0.2 g of 10% palladium on carbon was shaken in a Paar apparatus at 40 p.s.i.g. hydrogen at ambient temperature. After twenty-four hours, no further pressure drop was observed. The reaction mixture was filtered and the filtrate stripped to yield a small amount of the desired product. The solids which contained most of the product and catalyst, were stirred with 20 ml of 5% aqueous sodium hydroxide, filtered and the filtrate combined with the residue from the acetic acid filtrate. After refiltering the resultant alkaline solution, it was acidified to pH 3 with dilute hydrochloric acid to precipitate the desired compound. After filtration and drying, the compound, when heated to 160°, underwent a transformation in physical appearance and subsequently melted at 210°-215°. The infrared absorption pressure for the compound showed absorption peaks at 3300 and 3400 cm-1, consistent for an amino substituent, and absorption bands at 1700, 1690, 1600 and 1550 cm-1 which are consistent for the amino-carbonyl sulfonamide function. The product thus obtained was sufficiently pure for the purposes of this invention.

Workup

  1. customat ambient temperature
  2. waitAfter twenty-four hours
  3. filtrationThe reaction mixture was filtered

Sources & evidence

ORD record
ord-ac3509cb050c4bfd8745ebd2306201d4
Source dataset
uspto-grants-1983_01
Patent number
US04369058

Reaction notes

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