4-Nitrobenzoyl chloride → Disodium

HRID 436369Notes

Reaction equation

HRID 436369 reaction equation
[NH2:1][C:2]1[C:3]([N:17]=[N:18][C:19]2[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][C:20]=2[S:26]([OH:29])(=[O:28])=[O:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([OH:15])(=[O:14])=[O:13])[CH:6]=[C:5]2[OH:16].[Na:30][Na:31].[OH-].[Na+].[N+:34]([C:37]1[CH:45]=[CH:44][C:40]([C:41](Cl)=[O:42])=[CH:39][CH:38]=1)([O-:36])=[O:35]>CCOCC.C(O)(=O)C>[NH2:1][C:2]1[C:3]([N:17]=[N:18][C:19]2[CH:24]=[CH:23][C:22]([NH:25][C:41](=[O:42])[C:40]3[CH:39]=[CH:38][C:37]([N+:34]([O-:36])=[O:35])=[CH:45][CH:44]=3)=[CH:21][C:20]=2[S:26]([OH:29])(=[O:28])=[O:27])=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([S:12]([OH:15])(=[O:14])=[O:13])[CH:6]=[C:5]2[OH:16].[Na:30][Na:31]

Participants

8

Reactant 4

HCID 85024-Nitrobenzoyl chlorideHCID 14798Sodium HydroxideHCID 80696HCID 80696, compoundHCID 141233Disodium

Product 2

HCID 141233DisodiumHCID 136354662HCID 136354662, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherCatalystHCID 176Acetic AcidSolvent

Procedure

A solution of 2.0 g of 6-amino-5-(4-amino-2-sulfophenylazo)-4-hydroxy-2-naphthalenesulfonic acid, disodium salt in 14.0 ml of N sodium hydroxide is treated with 2.0 g of p-nitrobenzoyl chloride and a few drops of ether. The reaction mixture is shaken for 3 to 4 minutes and then another 7 ml portion of base is added to the reaction mixture. After shaking for 15 minutes the procedure is repeated with an additional 7 ml portion of base. Finally the reaction mixture is acidified with 2 ml of glacial acetic acid, and extracted several times with ether. After the ethereal layer is separated the aqueous phase is salted with 20 g of sodium acetate trihydrate at 55° C with stirring. The reaction mixture is filtered after standing overnight at room temperature and washed with absolute ethanol and ether to give 6-amino-4-hydroxy-5-[4-(p-nitrobenzamido)-2-sulfophenylazo]-2-naphthalenesulfonic acid, disodium salt.

Workup

  1. additionanother 7 ml portion of base is added to the reaction mixture
  2. stirringAfter shaking for 15 minutes the procedure
  3. extractionextracted several times with ether
  4. customAfter the ethereal layer is separated the aqueous phase
  5. customis salted with 20 g of sodium acetate trihydrate at 55° C
  6. stirringwith stirring
  7. filtrationThe reaction mixture is filtered
  8. waitafter standing overnight at room temperature
  9. washwashed with absolute ethanol and ether

Sources & evidence

ORD record
ord-fd58caefbe2d4ef5ba56ef3bd3b3825f
Source dataset
uspto-grants-1977_02
Patent number
US04008320

Reaction notes

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