Hydrochloric Acid → HCID 178514500, compound

HRID 1287181

Reaction equation

HRID 1287181 reaction equation
[N+:1](=[C:3]1[CH:12]=[CH:11][C:10]2[C:9]([S:13](Cl)(=[O:15])=[O:14])=[CH:8][CH:7]=[CH:6][C:5]=2[C:4]1=[O:17])=[N-:2].[K].[OH:19][C:20]1[CH:25]=[CH:24][C:23]([N:26]=[N+:27]=[N-:28])=[CH:22][CH:21]=1.Cl>O1CCOCC1.O>[N+:1](=[C:3]1[CH:12]=[CH:11][C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[S:13]([O:19][C:20]2[CH:25]=[CH:24][C:23]([N:26]=[N+:27]=[N-:28])=[CH:22][CH:21]=2)(=[O:15])=[O:14])[C:4]1=[O:17])=[N-:2]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 5462222PotassiumHCID 116223404-AzidophenolHCID 1363787716-Diazo-5,6-dihydro-5-oxo-1-naphthalenesulfonyl chloride

Product 1

HCID 178514500HCID 178514500, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent2×

Procedure

1,2-Dihydro-2-diazo-1-oxo-naphthalene-5-sulfonyl chloride (2.2 grams) is dissolved in dioxane (16 mls.) and the potassium salt of 4-hydroxyphenylazide (1.6 grams) in a mixture of water (4 ml.) and dioxane (4 ml.) is added gradually over a period of 10 minutes with stirring. The mixture is then stirred at room temperature (22°C) for 30 minutes to complete the reaction and then diluted with water (60 ml.) containing 3N hydrochloric acid (8 ml.). An oil separates out which solidifies on standing. The product is then collected and dried (2.5 grams). It is dissolved in benzene treated with carbon and filtered. Addition of 60°-80° pet. ether to the filtrate yields Compound 1. (1.7 grams) m.p. 136°-7° with decomposition.

Workup

  1. additionis added gradually over a period of 10 minutes
  2. stirringThe mixture is then stirred at room temperature (22°C) for 30 minutes
  3. customthe reaction
  4. customThe product is then collected
  5. customdried (2.5 grams)
  6. dissolutionIt is dissolved in benzene
  7. additiontreated with carbon
  8. filtrationfiltered
  9. additionAddition of 60°-80° pet. ether to the filtrate

Sources & evidence

ORD record
ord-f4cc612eb84048d6b312db1ce99d7ea5
Source dataset
uspto-grants-1976_10
Patent number
US03984250

Linked notes

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