Hydrochloric Acid → HCID 12922648, compound

HRID 1277425Notes

Reaction equation

HRID 1277425 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:12]2[CH:17]=[CH:16][C:15]([S:18]([O-:21])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].[Na+].Cl>C(O)C>[N+:1]([C:4]1[CH:5]=[C:6]([CH2:10][N:11]([CH2:22][C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([N+:29]([O-:31])=[O:30])[CH:24]=2)[C:12]2[CH:13]=[CH:14][C:15]([S:18]([OH:21])(=[O:19])=[O:20])=[CH:16][CH:17]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 12922647HCID 12922647, compound

Product 1

HCID 12922648HCID 12922648, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 25.75 grams (g) (0.15 mole) of sulfanilic acid in 450 milliliters (ml) of water, 37 g (0.46 mole) of 50 percent sodium hydroxideand 58.3 g (0.34 mole) of 3-nitrobenzyl chloride was stirred and heated to about 90° C. for 31/2 hours, during which time the reaction mixtureturned from a milky yellow to a reddish brown color. The solution was allowed to cool overnight and the resulting solid isolated by vacuum filtration. The solid was washed thoroughly with diethyl ether to remove excess 3-nitrobenzyl chloride, leaving 20.0 g of sodium 4-(bis((3-nitrophenyl)methyl)-amino)benzenesulfonate as shiny, yellow flakes having a melting point greater than 275° C. A 14.7 g portionof the sodium 4-(bis((3-nitrophenyl)methyl)amino)-benzenesulfonate was heated to 65° C. in approximately 350 ml of absolute ethanol and then acidified with concentrated hydrochloric acid. Upon cooling to room temperature, a solid crystallized which was recovered by vacuum filtrationto give 10.0 g of 4-(bis((3-nitrophenyl)methyl)amino)benzenesulfonic acid as light tan crystals which decomposed at 226°-228° C.

Workup

  1. customa solid crystallized which
  2. filtrationwas recovered by vacuum filtrationto

Sources & evidence

ORD record
ord-22a54feb96bc4ebab85b9826347dbfc1
Source dataset
uspto-grants-1981_07
Patent number
US04277492

Reaction notes

Loading…