Hydrochloric Acid → HCID 136355258, compound

HRID 2109966Notes

Reaction equation

HRID 2109966 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([CH3:21])[CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18])=[CH:10][CH:9]=1.Cl.[N:23]([O-])=O.[Na+].[CH:27]1[C:36]2[C:31](=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:30]=[CH:29][C:28]=1[OH:37].C(=O)([O-])[O-].[Na+].[Na+]>O.NS(O)(=O)=O.C(O)(C)C>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[OH:37][C:28]1[CH:29]=[CH:30][C:31]2[C:36](=[CH:35][CH:34]=[CH:33][CH:32]=2)[C:27]=1[N:23]=[N:7][C:8]1[CH:9]=[CH:10][C:11]([N:14]([CH3:21])[CH2:15][CH2:16][N+:17]([CH3:20])([CH3:19])[CH3:18])=[CH:12][CH:13]=1

Participants

9

Reactant 5

HCID 313Hydrochloric Acid2×HCID 86632-NaphtholHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 86760851HCID 86760851, compound

Product 1

HCID 136355258HCID 136355258, compound

Reagents, catalysts & solvents 3

HCID 5987Sulfamic AcidCatalystHCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

1.6 g (5 mmol) of the compound from Step 9.3 was dissolved in 20 mL of water and 1.7 g of hydrochloric acid (32%) and to the solution was added dropwise with agitation, in an ice bath, 0.35 g (5 mmol) of sodium nitrite in 2 mL of water. The mixture was allowed to agitate in the ice bath for an additional 30 minutes after which a few drops of 10% sulfaminic acid solution was added and the mixture was poured into a solution of 0.72 g (5 mmol) of 2-naphthol in 8 mL of isopropanol. The pH was then increased to 9 by addition of saturated sodium carbonate solution which resulted in the formation of a brown solution. After 30 min, the mixture was neutralized by addition of 2-normal hydrochloric acid and, to isolate the dye, evaporated to dryness in a rotary evaporator. The residue was then taken up in 80 mL of methanol, the inorganic salts were filtered off and the solution was concentrated to a total volume of about 10 ml. The addition of about 30 mL of isopropanol caused the dye to precipitate.

Workup

  1. additionwas added
  2. customresulted in the formation of a brown solution
  3. customto isolate the dye
  4. customevaporated to dryness in a rotary evaporator
  5. filtrationthe inorganic salts were filtered off
  6. concentrationthe solution was concentrated to a total volume of about 10 ml
  7. additionThe addition of about 30 mL of isopropanol
  8. customto precipitate

Sources & evidence

ORD record
ord-09675eaeb0514f20bb1515eeaac5ac6b
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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