2,3,4-Trinitrobenzene-1-sulfonic acid → Nitrobenzene

HRID 34684Notes

Reaction equation

HRID 34684 reaction equation
CC1C2=CC=CC(C(O[C@H]3[C@H](O[C@H]4O[C@H](C)[C@H](O)[C@H](O)[C@H]4NC)C4=CC#C[C@H]5O[C@@]5([C@@H]5OC(=O)OC5)C#CC4=C3)=O)=C2C=C(OC)C=1.[N+:48]([C:51]1[CH:56]=[CH:55][C:54](S(O)(=O)=O)=[C:53]([N+]([O-])=O)[C:52]=1[N+]([O-])=O)([O-:50])=[O:49]>C(=O)(O)[O-].[Na+]>[N+:48]([C:51]1[CH:56]=[CH:55][CH:54]=[CH:53][CH:52]=1)([O-:50])=[O:49]

Participants

4

Reactant 2

HCID 197770232,3,4-Trinitrobenzene-1-sulfonic acidHCID 44581473[(4S,6R,9E,11R,12R)-11-[(2R,3R,4R,5R,6R)-4,5-dihydroxy-6-methyl-3-(methylamino)oxan-2-yl]oxy-4-[(4R)-2-oxo-1,3-dioxolan-4-yl]-5-oxatricyclo[8.3.0.04,6]trideca-1(13),9-dien-2,7-diyn-12-yl] 7-methoxy-5-methylnaphthalene-1-carboxylate2×

Product 1

HCID 7416Nitrobenzene

Reagents, catalysts & solvents 1

HCID 516892Sodium BicarbonateSolvent

Procedure

20 g of neocarzinostatin (NCS) was dissolved in 5.0 ml of 0.8M aqueous solution of sodium bicarbonate under ice-cooling in the dark. The powdery H-SMA stepwise was added in a total amount of 0.5 g in several times and dissolved thereinto. During the reaction,, the pH of the solution was kept around 8.5. The conversion of such an unreacted primary amino group originating from NCS can be determined by a method (hereinafter referred to as "TNBS" method) in which a small amount of a sample taken out from the reaction mixture 24 hours after the addition was started was diluted, and was reacted with trinitrobenzene sulfonic acid to produce a nitrobenzene derivative, which was determined based on the amount of the primary amino group spectrophotometrically by a visible absorption spectrometer at 420 nm. It was learned that the primary amino groups completely disappeared.

Workup

  1. temperaturecooling in the dark
  2. additionThe powdery H-SMA stepwise was added in a total amount of 0.5 g in several times
  3. dissolutiondissolved
  4. customDuring the reaction
  5. customtaken out from the reaction mixture 24 hours
  6. additionafter the addition
  7. additionwas started was diluted

Sources & evidence

ORD record
ord-848710d220bc4c5490edc2a5d4fa3c38
Source dataset
uspto-grants-1988_08
Patent number
US04762885

Reaction notes

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