O-Phenylenediamine → HCID 67005049, compound

HRID 563984Notes

Reaction equation

HRID 563984 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[CH2:9][NH:10][C:11]#[N:12].[C:13]1(N)[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1[NH2:19]>C(O)(C(F)(F)F)C(F)(F)F>[ClH:1].[NH:12]1[C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2[N:19]=[C:11]1[NH:10][CH2:9][C:3]1[C:2]([Cl:1])=[CH:7][CH:6]=[CH:5][C:4]=1[Cl:8]

Participants

4

Reactant 2

HCID 7243O-PhenylenediamineHCID 12728428HCID 12728428, compound

Product 1

HCID 67005049HCID 67005049, compoundYield 4.1%

Reagents, catalysts & solvents 1

HCID 135291,1,1,3,3,3-Hexafluoro-2-propanolSolvent

Conditions

Temperature
100 °C

Procedure

(2,6-Dichlorophenyl)methylcyanamide (150 mg) and phenylenediamine (81 mg) were dissolved in hexafluoro-2-propanol (1 ml) and heated at 100° C. in a closed vessel for 2 days. After a further day at 60° C. in an open vessel, the solvent was removed and the residue was purified by preparative HPLC. The product-containing fractions were combined, the acetonitrile was stripped off in a rotary evaporator, and the aqueous residue was neutralized with potassium carbonate and extracted three times with ethyl acetate. Drying over magnesium sulfate and purification with carbon were followed by evaporation to dryness. The residue was taken up in aqueous hydrochloric acid and freeze dried. 5 mg of the desired compound were obtained.

Workup

  1. waitAfter a further day at 60° C. in an open vessel
  2. customthe solvent was removed
  3. customthe residue was purified by preparative HPLC
  4. customthe acetonitrile was stripped off in a rotary evaporator
  5. extractionextracted three times with ethyl acetate
  6. dry with materialDrying over magnesium sulfate and purification with carbon
  7. customwere followed by evaporation to dryness
  8. customfreeze dried

Sources & evidence

ORD record
ord-753bda09336a49a899a3a415dcf213c3
Source dataset
uspto-grants-2011_11
Patent number
US08067614B2

Reaction notes

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