Ammonia → HCID 20393029, compound

HRID 1862973Notes

Reaction equation

HRID 1862973 reaction equation
Cl[C:2]1[N:10]=[C:9]([CH3:11])[CH:8]=[C:7]([CH3:12])[C:3]=1[C:4]([OH:6])=O.[CH3:13][C:14]1[C:19]([CH3:20])=[CH:18][C:17]([NH2:21])=[C:16]([NH2:22])[CH:15]=1.N>S1(CCCC1)(=O)=O>[CH3:11][C:9]1[CH:8]=[C:7]([CH3:12])[C:3]2[C:4](=[O:6])[NH:22][C:16]3[CH:15]=[C:14]([CH3:13])[C:19]([CH3:20])=[CH:18][C:17]=3[NH:21][C:2]=2[N:10]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 766354,5-Dimethyl-1,2-phenylenediamineHCID 5911272-Chloro-4,6-dimethylnicotinic acid

Product 1

HCID 20393029HCID 20393029, compound

Reagents, catalysts & solvents 1

HCID 31347SulfolaneSolvent

Conditions

Temperature
220 °C

Procedure

A mixture consisting of 52.0 gm of 2-chloro-4,6-dimethyl-nicotinic acid, 38.0 gm of 4,5-dimethyl-o-phenylenediamine and 150 ml of sulfolane was heated on an oil bath at 220° C. After 45 minutes the mixture was allowed to cool to 100° C. and was then poured over ice. After neutralization with ammonia and standing for several hours the precipitate which had formed was suction-filtered off and admixed with dilute acetic acid. The mixture was suction-filtered after one hour, and the filter cake was recrystallized from aqueous 80% acetic acid, yielding 34% of theory of the compound named in the heading, which had a melting point of 264°-268° C.

Workup

  1. temperatureto cool to 100° C.
  2. additionwas then poured over ice
  3. customthe precipitate which had formed
  4. filtrationwas suction-filtered off
  5. filtrationThe mixture was suction-filtered after one hour
  6. customthe filter cake was recrystallized from aqueous 80% acetic acid
  7. customyielding 34% of theory of the compound

Sources & evidence

ORD record
ord-9547794dcb7d42eda3c9e4a7a9e90984
Source dataset
uspto-grants-1979_09
Patent number
US04167570

Reaction notes

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