Acetic Acid → HCID 178478160, compound

HRID 1602292Notes

Reaction equation

HRID 1602292 reaction equation
[NH2:1][C:2]1[NH:6][N:5]=[C:4]([NH:7][C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=2)[C:3]=1[C:15]#[N:16].[CH2:17]([NH2:24])[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.[C:25](O)(=O)C.C(O)=O>C(O)C>[CH2:17]([NH:24][C:15]1[N:16]=[CH:25][N:1]=[C:2]2[NH:6][N:5]=[C:4]([NH:7][C:8]3[CH:13]=[CH:12][CH:11]=[C:10]([Cl:14])[CH:9]=3)[C:3]=12)[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 284Formic AcidHCID 7504BenzylamineHCID 106811675-Amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole

Product 1

HCID 178478160HCID 178478160, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
200 °C

Procedure

A mixture of 1 g (4.28 mmol) of 5-amino-3-(3-chloro-phenylamino)-4-cyano-pyrazole (Step 49.1), 3.67 g (34.25 mmol) of benzylamine, 0.245 ml (4.28 mmol) of glacial acetic acid and 0.73 ml (19.35 mmol) of formic acid is heated at 200° C. for 20 hours. The reaction mixture is cooled to RT, 30 ml of ice-water and 5 ml of ethanol are added and stirring is carried out for a further 20 minutes. The reaction mixture is then filtered and the filter residue is washed with water. Recrystallization from isopropyl alcohol yields the title compound; m.p. 215-218° C.

Workup

  1. temperatureThe reaction mixture is cooled to RT
  2. filtrationThe reaction mixture is then filtered
  3. washthe filter residue is washed with water
  4. customRecrystallization from isopropyl alcohol

Sources & evidence

ORD record
ord-fa79d5a82f7a403eb5e17f93179d91dd
Source dataset
uspto-grants-1999_11
Patent number
US05981533

Reaction notes

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