Hydrochloric Acid → HCID 178419882, compound

HRID 1863066Notes

Reaction equation

HRID 1863066 reaction equation
C=CC1C=CC=CC=1.Cl.N([O-])=O.[Na+].[N:14](O)=O.N[C:18]([NH2:20])=O.[NH2:21][C:22]1[CH:31]=[CH:30][C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)C=1>C([O-])(=O)C.[Cu+2].C([O-])(=O)C.N1C=CC=CC=1.O.CN(C)C=O.COCCO>[NH:20]1[C:18]2[C:24]3[C:29]([CH:30]=[CH:31][C:22]=2[N:21]=[N:14]1)=[CH:28][CH:27]=[CH:26][CH:25]=3

Participants

12

Reactant 6

HCID 313Hydrochloric AcidHCID 1176UreaHCID 70572-NaphthylamineHCID 7501StyreneHCID 24529Nitrous AcidHCID 23668193Sodium Nitrite

Product 1

HCID 178419882HCID 178419882, compound

Reagents, catalysts & solvents 5

HCID 8895Cupric acetateCatalystHCID 962WaterSolvent2×HCID 1049PyridineSolvent2×HCID 6228DimethylformamideSolventHCID 80192-MethoxyethanolSolvent

Procedure

10 Parts of 4-amino-β-[2'-4"-cyanophenyloso)triazolyl]-styrene are mixed with 30 parts of 2-methoxyethanol and 11 parts of dimethyl formamide with cooling to 5°, then 15 parts of 35% hydrochloric acid, 40 parts of water, 30 parts of ice and a solution of 3 parts of sodium nitrite in 10 parts of water are added consecutively. The suspension is stirred at 5° until diazotization is complete, then the small excess of nitrous acid is decomposed with urea. A solution of 5 parts of 2-aminonaphthalene in 50 parts of pyridine is added to the well stirred suspension of the diazonium salt. The product is 15 parts of a red-brown compound, melting point in the crude state 150°-160°. The compound is suspended in 50 parts of pyridine along with 7.5 parts of crystallized copper acetate, the suspension raised to 105° and held at this temperature for 2 hours with the introduction of a powerful air stream. 10 Parts of a yellow naphthotriazole compound are obtained, which after recrystallization from 600 parts of chlorobenzene melts at 292°-294°. This compound has the formula Id, ##STR16## Its absorption maximum in chloroform is at 370 nm and in chlorobenzene solution it exhibits pronounced redviolet fluorescence (Fem 427 nm).

Workup

  1. temperaturewith cooling to 5°
  2. stirringstirred
  3. customstate 150°-160°
  4. temperaturethe suspension raised to 105°

Sources & evidence

ORD record
ord-c54fbc140b7c45b7a473b42ce5f47d9f
Source dataset
uspto-grants-1979_09
Patent number
US04167629

Reaction notes

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