Dimethyl Sulfoxide → HCID 22715291, compound

HRID 48870

Reaction equation

HRID 48870 reaction equation
[NH:1]([C:5]1[CH:14]=[CH:13][C:8]([C:9](=[O:12])[CH2:10][Cl:11])=[CH:7][CH:6]=1)C(C)=O.[N:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1.CS(C)=O>CCOCC>[ClH:11].[Cl-:11].[NH2:1][C:5]1[CH:6]=[CH:7][C:8]([C:9](=[O:12])[CH2:10][N+:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 679Dimethyl Sulfoxide2×HCID 1049Pyridine2×HCID 88054'-Chloroacetyl(acetanilide)

Product 1

HCID 22715291HCID 22715291, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A solution of 2.12 g of 4-acetaminophenacyl chloride, 0.83 g of pyridine, and 6.4 g of dimethyl sulfoxide was agitated for one night. 0.8 g of pyridine and 1 g of dimethyl sulfoxide were further added, and thereafter, the resulting solution was further agitated for 5 hours. 50 mL of ether was added, and acetamidophenacylpyridinium chloride was separated by filtration. The separated acetamidophenacylpyridinium chloride was dissolved into water, and the resulting solution was filtered, and thereafter, 1.7 g of concentrated nitric acid was added. The resulting solution was boiled for one hour, and after cooling, acetone was added. Then, 4-aminophenacylpyridinium chloride hydrochloride was produced by filtration. 2 g of the resulting 4-aminophenacylpyridinium chloride hydrochloride was dissolved into 15 g of water, and 4.5 g of basic ion-exchange resin (Amberlite IRA400-OH) was added. After agitation, the ion-exchange resin was removed by filtration so as to produce an aqueous solution of 4-aminophenacylpyridinium chloride. An aqueous solution of 25 g of water and 1.3 g of 4-aminophenacylpyridinium chloride was refluxed with 1 g of silver nitrate for 90 minutes. Generated precipitates were removed by filtration. Then, 5 g of carbon black having a specific surface area of 200 m2/g and DBPA of 122 mL/100 g was added, and the resulting mixture was heated to about 80° C. 0.52 g of concentrated hydrochloric acid was added, and thereafter, a solution of small amounts of water and sodium nitrite was added. Furthermore, the disperse liquid was agitated for 1.5 hours. As a consequence, a diazonium salt including NN+C6H4COCH2(N+C5H5) group having the following structure was produced and was reacted with carbon black. As a result, a product in which C6H4COCH2(N+C5H5) group was bound to the surface of the carbon black was produced. The resulting carbon black powder was dispersed in water again, so as to produce a self-dispersing carbon black disperse material having a pigment content of 15%.

Workup

  1. customacetamidophenacylpyridinium chloride was separated by filtration
  2. dissolutionThe separated acetamidophenacylpyridinium chloride was dissolved into water
  3. filtrationthe resulting solution was filtered
  4. addition1.7 g of concentrated nitric acid was added
  5. waitThe resulting solution was boiled for one hour
  6. temperatureafter cooling
  7. additionacetone was added

Sources & evidence

ORD record
ord-7d7d1d3062a849a9a07a1eb8076d4871
Source dataset
uspto-grants-2004_03
Patent number
US06706105B2

Linked notes

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