Salicylic Acid → HCID 135510740, compound

HRID 1782110Notes

Reaction equation

HRID 1782110 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:12][S:11][C:10](=[S:13])[CH:9]=2)=[CH:4][CH:3]=1.[N:14]([O-])=O.[Na+].[C:18]([OH:27])(=[O:26])[C:19]1[C:20](=[CH:22][CH:23]=[CH:24][CH:25]=1)[OH:21].[OH-].[K+].C(=O)([O-])[O-].[Na+].[Na+]>Cl.O>[OH:21][C:20]1[CH:22]=[CH:23][C:24]([N:14]=[N:1][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[S:12][S:11][C:10](=[S:13])[CH:9]=3)=[CH:4][CH:3]=2)=[CH:25][C:19]=1[C:18]([OH:27])=[O:26]

Participants

8

Reactant 5

HCID 338Salicylic Acid2×HCID 10340Sodium CarbonateHCID 14797Potassium Hydroxide2×HCID 23668193Sodium NitriteHCID 57588558HCID 57588558, compound

Product 1

HCID 135510740HCID 135510740, compoundYield 85%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
50 °C

Procedure

5-(4-Amino-phenyl)-[1,2]dithiole-3-thione (3, 0.56 mmol) was dissolved in a mixture of 5 mL of concentrated HCl and 2.5 mL of water and diazotized with a solution of sodium nitrite (0.56 mmol). In the meantime salicylic acid (0.56 mmol), potassium hydroxide (1.12 mmol) and sodium carbonate are dissolved in water. The diazo suspension is added in portions to the alkaline solution of salicylic acid and the alkalinity maintained at a sufficiently high level during the whole reaction by means of addition of further quantities of potassium hydroxide solution. After 2 days the reaction mixture is heated for 30 min at 50° C. The azo compound (4) was precipitated by means of HCl and filtered off (yield 85%), to yield the compound of Formula II, 2-Hydroxy-5-[4-(5-thioxo-5H-[1,2]dithiol-3-yl)-phenylazo]-benzoic acid.

Workup

  1. customThe azo compound (4) was precipitated by means of HCl
  2. filtrationfiltered off (yield 85%)

Sources & evidence

ORD record
ord-bb25c0044288436ca48716586983b5a5
Source dataset
uspto-grants-2009_03
Patent number
US07498355B2

Reaction notes

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