Dimethylformamide → HCID 178482856, compound

HRID 1602261Notes

Reaction equation

HRID 1602261 reaction equation
[C:1]([C:3]1[C:4]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([N:20]([CH3:22])[CH3:21])=[CH:16][CH:15]=2)=[N:5][NH:6][C:7]=1[N:8]=[CH:9][N:10](C)C)#[N:2].Cl.[Cl:24][C:25]1[CH:26]=[C:27]([CH:29]=[CH:30][CH:31]=1)N.CN(C=O)C>O>[Cl:24][C:25]1[CH:31]=[C:30]([NH:2][C:1]2[N:10]=[CH:9][N:8]=[C:7]3[NH:6][N:5]=[C:4]([NH:13][C:14]4[CH:15]=[CH:16][C:17]([N:20]([CH3:21])[CH3:22])=[CH:18][CH:19]=4)[C:3]=23)[CH:29]=[CH:27][CH:26]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 178484266HCID 178484266, compound

Product 1

HCID 178482856HCID 178482856, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
130 °C

Procedure

A mixture of 5 g (16.8 mmol) of 4-cyano-5-(dimethylamino-methyleneamino)-3-(4-dimethylamino-phenylamino)-pyrazole, 3.3 g (20.1 mmol) of 3-chloro-aniline hydrochloride and 40 ml of DMF is heated for 8 hours, with stirring, at 130° C. The reaction mixture is then cooled to RT, water is added dropwise thereto, and the reaction mixture is then filtered and the filter residue is dissolved in approx. 20 ml of DMF. After precipitation with water, followed by recrystallization from DMF/water, the resulting crystals are suspended in 10 ml of water. 6 ml of 1N hydrochloric acid are added, the mixture is heated briefly to reflux and filtered and 3 ml of 2N sodium hydroxide solution are added to the filtrate. The crystalline precipitate is filtered off, washed with water and dried under a high vacuum at 120° C., yielding the title compound having a water content of 2.32%; m.p. 250-255° C. (decomp.).

Workup

  1. temperatureis heated for 8 hours
  2. temperatureThe reaction mixture is then cooled to RT
  3. filtrationthe reaction mixture is then filtered
  4. dissolutionthe filter residue is dissolved in approx. 20 ml of DMF
  5. customAfter precipitation with water
  6. customfollowed by recrystallization from DMF/water
  7. addition6 ml of 1N hydrochloric acid are added
  8. temperaturethe mixture is heated briefly
  9. temperatureto reflux
  10. filtrationfiltered
  11. addition3 ml of 2N sodium hydroxide solution are added to the filtrate
  12. filtrationThe crystalline precipitate is filtered off
  13. washwashed with water
  14. customdried under a high vacuum at 120° C.

Sources & evidence

ORD record
ord-a43027c728b6415da8e109573eb49c54
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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