Hydrochloric Acid → HCID 136399863, compound

HRID 2109955Notes

Reaction equation

HRID 2109955 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][CH2:12][N+:13]([CH3:16])([CH3:15])[CH3:14].Cl.N([O-])=O.[Na+].N([O-])=O.[NH2:29]S(O)(=O)=O.[CH:34]1[C:43]2[C:38](=[CH:39][CH:40]=[CH:41][CH:42]=2)[CH:37]=[CH:36][C:35]=1[OH:44].C(=O)([O-])[O-].[Na+].[Na+]>O.C(O)(C)C>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[OH:44][C:35]1[CH:36]=[CH:37][C:38]2[C:43](=[CH:42][CH:41]=[CH:40][CH:39]=2)[C:34]=1[N:29]=[N:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[O:10][CH2:11][CH2:12][N+:13]([CH3:16])([CH3:14])[CH3:15]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 946NitriteHCID 5987Sulfamic AcidHCID 86632-NaphtholHCID 10340Sodium CarbonateHCID 23668193Sodium NitriteHCID 86621482HCID 86621482, compound

Product 1

HCID 136399863HCID 136399863, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

15.6 g (50 mmol) of the compound obtained in Step 1.1 was dissolved in 160 mL of water and 18.3 g of a 32% hydrochloric acid solution, and the resulting mixture was diazotized with 4.2 g (60 mmol) of sodium nitrite in 25 mL of water with cooling in an ice bath while keeping the temperature from exceeding 5° C. The mixture was allowed to agitate for an additional hour after which excess nitrite was decomposed by addition of sulfaminic acid. The diazonium salt solution was then poured into a solution of 7.4 g (51 mmol) of 2-naphthol in 50 mL of isopropanol with agitation. The pH was adjusted to 9 to 10 by addition of saturated sodium carbonate solution which brought about coupling with formation of a thick dye slurry. Agitation was continued for an additional 30 minutes after which the mixture was suction-filtered. The crude product was then taken up in 300 mL of 60° C. water, neutralized with 2-normal hydrochloric acid, cooled and again suction-filtered. Drying gave 13 g (55% of the theoretical) of a red product.

Workup

  1. temperaturewith cooling in an ice bath
  2. customfrom exceeding 5° C
  3. filtrationafter which the mixture was suction-filtered
  4. customwas then taken up in 300 mL of 60° C. water
  5. temperaturecooled
  6. filtrationagain suction-filtered
  7. customDrying
  8. customgave 13 g (55% of the theoretical) of a red product

Sources & evidence

ORD record
ord-30cec2b71fd64eddab10dfe5c5b0e799
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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