Hydrochloric Acid → HCID 13007213, compound

HRID 51236Notes

Reaction equation

HRID 51236 reaction equation
N[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[C:10]([O:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35])=[CH:11][C:12]2[C:25]3[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=3C(=O)[C:18]3[C:13]=2[C:14]=1[CH:15]=[CH:16][CH:17]=3.CN([CH:39]=[O:40])C.Cl.N([O-])=O.[Na+]>O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:28]([O:27][C:10]1[CH:11]=[C:12]2[C:25]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:39](=[O:40])[C:18]3[CH:17]=[CH:16][C:15]4[C:4]5[C:3]([S:8][C:9]=1[C:14]=4[C:13]2=3)=[CH:2][CH:7]=[CH:6][CH:5]=5)[CH2:29][CH2:30][CH2:31][CH2:32][CH2:33][CH2:34][CH3:35]

Participants

7

Reactant 4

HCID 313Hydrochloric Acid2×HCID 6228DimethylformamideHCID 13007212HCID 13007212, compoundHCID 23668193Sodium Nitrite2×

Product 1

HCID 13007213HCID 13007213, compound

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 962WaterSolvent

Conditions

Temperature
10 °C

Procedure

Into a 2 liter three-necked round bottom flask, equipped with a mechanical stirrer and a thermometer, containing 77 g 3-[(2-aminophenyl)thio]-2-n-octyloxy-7H-benzo[de]anthracene-7-one (0.16M), placed into an ice bath, was added 1100 ml of DMF. The mixture was cooled to 10° C. while stirring. 35% Hydrochloric acid (247 ml) was added portionwise, ensuring that the reaction temperature did not exceed 20° C. After the HCl addition was complete, the reaction was cooled to 0° C. and a solution of 14.0 g (0.2M) NaNO2 in 78 ml of H2O was added portionwise, making sure that the reaction temperature did not rise above 5° C. The reaction mixture was held at 5° C. for an additional 1 hour after the completion of the sodium nitrite addition. Then, during the addition of 5.2 g copper sulfate catalyst, the reaction was heated, and at 15° C., nitrogen bubbles began to evolve. The reaction mass was held at 100° C. for 1.5 hours, cooled and the red colored precipitate was filtered and washed with water, then ethanol. The yield=66.89 g (90%); Tm=205-208° C.

Workup

  1. customInto a 2 liter three-necked round bottom flask, equipped with a mechanical stirrer
  2. customplaced into an ice bath
  3. customdid not exceed 20° C
  4. temperaturethe reaction was cooled to 0° C.
  5. customdid not rise above 5° C
  6. temperaturethe reaction was heated
  7. customat 15° C.
  8. waitThe reaction mass was held at 100° C. for 1.5 hours
  9. temperaturecooled
  10. filtrationthe red colored precipitate was filtered
  11. washwashed with water
  12. customTm=205-208° C.

Sources & evidence

ORD record
ord-c28fabd80c044dafa392eaf541195aad
Source dataset
uspto-grants-2004_03
Patent number
US06713636B2

Reaction notes

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