Sodium Acetate → HCID 135749779, compound

HRID 326972Notes

Reaction equation

HRID 326972 reaction equation
[N:1]([O-])=O.[Na+].[S:5]([O:9][C:10]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:11]=1[NH2:12])([CH3:8])(=[O:7])=[O:6].[NH2:20][C:21]1[C:26]([OH:27])=[CH:25][C:24]([S:28](=[O:34])(=[O:33])[NH:29][CH:30]([CH3:32])[CH3:31])=[CH:23][N:22]=1.C([O-])(=O)C.[Na+]>S(=O)(=O)(O)O.CC(OCC1C2C(=CC=CC=2)C(COC(C)=O)=C2C=1C=CC=C2)=O.C(O)(=O)C.O>[NH2:20][C:21]1[C:26]([OH:27])=[CH:25][C:24]([S:28](=[O:34])(=[O:33])[NH:29][CH:30]([CH3:31])[CH3:32])=[C:23]([N:1]=[N:12][C:11]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:10]=2[O:9][S:5]([CH3:8])(=[O:7])=[O:6])[N:22]=1

Participants

9

Reactant 4

HCID 517045Sodium AcetateHCID 19734132HCID 19734132, compoundHCID 19734137HCID 19734137, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 135749779HCID 135749779, compound

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 1118Sulfuric AcidSolventHCID 613145Acetic acid 10-acetoxymethyl-anthracen-9-ylmethyl esterSolvent

Procedure

Sodium nitrite (3.6 g) was dissolved in concentrated sulfuric acid (25 ml) with slight warming. After cooling the solution was diluted with a mixture of acetic and propionic acids (5/1 50 ml). 2-Mesyloxy- 4-nitroaniline (11.6 g) was added portionwise with vigorous stirring. After 2 hours another portion of 5/1 acid was added and the diazonium solution kept at 5° C. while a solution of 2-amino-3-hydroxy-5-isopropylsulfamoylpyridine (11.5 g) in aqueous acetic acid (1/1 500 ml) containing sodium acetate (100 g) was being prepared. The diazonium solution was slowly added to the coupler solution at 5° C. and the reaction mixture stirred for 1 hour and then diluted with water. The dye was filtered off washed with a large volume of water and dried in a vacuum oven. Yield 26.8 g of the desired material and some inorganic salts.

Workup

  1. temperatureAfter cooling the solution
  2. additionAfter 2 hours another portion of 5/1 acid was added
  3. customwas being prepared
  4. filtrationThe dye was filtered off
  5. washwashed with a large volume of water
  6. customdried in a vacuum oven

Sources & evidence

ORD record
ord-4c99c51c5b554f818c3f4782958d02f8
Source dataset
uspto-grants-1993_12
Patent number
US05272047

Reaction notes

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