Benzenamine, 3-chloro-, hydrochloride (1:1) → HCID 135772615, compound

HRID 1602267Notes

Reaction equation

HRID 1602267 reaction equation
[C:1]([C:3]1[C:4]([NH:13][CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=2)=[N:5][NH:6][C:7]=1[N:8]=[CH:9][N:10]([CH3:12])C)#[N:2].Cl.[Cl:24][C:25]1[CH:26]=C([CH:29]=[CH:30][CH:31]=1)N>C(O)C>[ClH:24].[Cl:24][C:25]1[CH:26]=[C:12]([N:10]2[C:1](=[NH:2])[C:3]3[C:4]([NH:13][CH2:14][C:15]4[CH:20]=[CH:19][CH:18]=[C:17]([O:21][CH3:22])[CH:16]=4)=[N:5][NH:6][C:7]=3[N:8]=[CH:9]2)[CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 67336Benzenamine, 3-chloro-, hydrochloride (1:1)HCID 54268353HCID 54268353, compound

Product 1

HCID 135772615HCID 135772615, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
10 °C

Procedure

A mixture of 5.97 g (20 mmol) of 4-cyano-5-(dimethylamino-methyleneamino)-3-(3-methoxy-benzylamino)-pyrazole, 3.77 g (23 mmol) of 3-chloro-aniline hydrochloride and 100 ml of ethanol is heated under reflux for 36 hours. Cooling to approx. 10° C., filtering and washing the filter residue with ethanol yield title compound II; m.p. 251-253° C. (decomp.). The filtrate is concentrated by evaporation in vacuo, the oily residue is partitioned between ethyl acetate and water and the organic phase is washed with brine, dried over sodium sulfate and concentrated to a volume of approx. 25 ml using an RV, a crystalline precipitate being formed. Filtering and washing the filter residue with a small amount of ethyl acetate and diethyl ether yield title compound I (see Example 52); m.p. 194-195° C.

Workup

  1. temperatureis heated
  2. temperatureunder reflux for 36 hours
  3. filtrationfiltering
  4. washwashing the filter residue with ethanol

Sources & evidence

ORD record
ord-f5b0e0766e004726bec97a6dd860c4b5
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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