Hydrochloric Acid → Disodium

HRID 1074438Notes

Reaction equation

HRID 1074438 reaction equation
[NH2:1][C:2]1[C:3]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([OH:12])[CH:8]=[C:7]([S:13]([OH:16])(=[O:15])=[O:14])[CH:6]=2.O.O.O.C([O-])(=O)C.[Na+:28].[N+:29]([C:32]1[CH:33]=[C:34]([CH:38]=[CH:39][CH:40]=1)[C:35](Cl)=[O:36])([O-:31])=[O:30].[OH-].[Na+:42].Cl>O.C(OCC)C>[OH:12][C:9]1[CH:8]=[C:7]([S:13]([OH:16])(=[O:15])=[O:14])[CH:6]=[C:5]2[C:10]=1[CH:11]=[C:2]([NH:1][C:35](=[O:36])[C:34]1[CH:38]=[CH:39][CH:40]=[C:32]([N+:29]([O-:31])=[O:30])[CH:33]=1)[C:3]([S:17]([OH:20])(=[O:19])=[O:18])=[CH:4]2.[Na:28][Na:42]

Participants

9

Reactant 5

HCID 313Hydrochloric AcidHCID 8495Benzoyl chloride, 3-nitro-HCID 14798Sodium Hydroxide3×HCID 666582,7-Naphthalenedisulfonic acid, 3-amino-5-hydroxy-HCID 23665404Sodium Acetate Trihydrate

Product 2

HCID 141233DisodiumHCID 20496770HCID 20496770, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Procedure

A 41.0 g portion of recrystallized 3-amino-5-hydroxy-2,7-naphthalenedisulfonic acid and 16.5 g of sodium acetate trihydrate are dissolved in 250 ml of distilled water, then 44.55 g of m-nitrobenzoyl chloride is added all at once along with 120 ml of 1 N sodium hydroxide and a small amount of diethyl ether. The resulting mixture is shaken for 5 minutes, another 120 ml of 1 N sodium hydroxide and a small amount of diethyl ether. The resulting mixture is shaken for 5 minutes, another 120 ml of 1 N sodium hydroxide is added and the mixture is shaken for 1/2 hour. The latter addition and shaking is repeated two more times. The resulting mixture is acidified to Congo Red indicator paper with concentrated hydrochloric acid and allowed to stand at 5° C. for 17 hours. The solution is filtered and the filtrate allowed to stand until a precipitate forms. The precipitate is stirred with about 400 ml of diethyl ether and collected to give 5-hydroxy-3-m-nitrobenzamido-2,7-naphthalenedisulfonic acid, disodium salt.

Workup

  1. stirringThe resulting mixture is shaken for 5 minutes
  2. stirringthe mixture is shaken for 1/2 hour
  3. additionThe latter addition
  4. stirringshaking
  5. waitto stand at 5° C. for 17 hours
  6. filtrationThe solution is filtered
  7. stirringThe precipitate is stirred with about 400 ml of diethyl ether
  8. customcollected

Sources & evidence

ORD record
ord-b8dec2aa45d946f1af0bfc63cf6aec12
Source dataset
uspto-grants-1983_07
Patent number
US04391824

Reaction notes

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