Hydrochloric Acid → HCID 136334700, compound

HRID 2109959Notes

Reaction equation

HRID 2109959 reaction equation
[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[NH2:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[CH3:19].Cl.N([O-])=O.[Na+].N([O-])=O.[NH2:32]S(O)(=O)=O.[CH:37]1[C:46]2[C:41](=[CH:42][CH:43]=[CH:44][CH:45]=2)[CH:40]=[CH:39][C:38]=1[OH:47].[OH-].[Na+]>O.C(O)(C)C>[CH3:1][O:2][S:3]([O-:6])(=[O:5])=[O:4].[OH:47][C:38]1[CH:39]=[CH:40][C:41]2[C:46](=[CH:45][CH:44]=[CH:43][CH:42]=2)[C:37]=1[N:32]=[N:7][C:8]1[CH:23]=[CH:22][CH:21]=[CH:20][C:9]=1[O:10][CH2:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][N+:14]=1[CH3:19]

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 946NitriteHCID 5987Sulfamic AcidHCID 86632-NaphtholHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 86760843HCID 86760843, compound

Product 1

HCID 136334700HCID 136334700, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 3776IsopropanolSolvent

Procedure

To the solution from Step 3.3 (10 mmol) was added 2.9 g of 32% hydrochloric acid solution. Then, in an ice bath, 0.7 g (10 mmol) of sodium nitrite dissolved in 5 mL of water was added dropwise over a period of 10 minutes without allowing the temperature to exceed 5° C. The mixture was allowed to agitate in the ice bath for an additional hour after which unreacted nitrite was decomposed by addition of sulfaminic acid. The resulting solution was then added to a solution of 1.45 g (10 mmol) of 2-naphthol in 15 mL of water, 15 mL of isopropanol and 3.4 g of 30% sodium hydroxide solution. The azo coupling took place spontaneously with formation of a thick, red slurry. The mixture was allowed to agitate for an additional hour after which it was suction-filtered. The resulting dye was dried at 40° C. under vacuum.

Workup

  1. additionwas added dropwise over a period of 10 minutes
  2. customto exceed 5° C
  3. filtrationwas suction-filtered
  4. customThe resulting dye was dried at 40° C. under vacuum

Sources & evidence

ORD record
ord-48d59228838945e991d1d9b7d32f038c
Source dataset
uspto-grants-2009_04
Patent number
US07517367B2

Reaction notes

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