Dichloromethane → HCID 18187300, compound

HRID 1357644Notes

Reaction equation

HRID 1357644 reaction equation
O.[N:2]1[C:15]2[C:6](=[N:7][C:8]3[C:13]([CH:14]=2)=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH:5]=[CH:4][CH:3]=1.C1C(=O)N([Cl:23])C(=O)C1.ClCCl>C(O)(C)C.C(OCC)(=O)C>[Cl:23][C:4]1[CH:3]=[N:2][C:15]2[C:6]([CH:5]=1)=[N:7][C:8]1[C:13](=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH:14]=2

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 31398ChlorosuccinimideHCID 86590614HCID 86590614, compound

Product 1

HCID 18187300HCID 18187300, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of the azaacridine hydrate 20 (100 mg, 0.33 mmol) and NCS (49 mg, 0.37 mmol) in isopropanol (5 mL) was refluxed for 15 minutes under nitrogen. The reaction was diluted with ethyl acetate (20 mL), washed with 1N HCl (3×10 mL) and saturated NaCl (5 mL), dried (MgSO4) and evaporated at reduced pressure giving a yellow powder. Trituration from dichloromethane and gave the 3-chloroazaacridine 21 as a creamy white crystalline powder, 102 mg (92%).

Workup

  1. washwashed with 1N HCl (3×10 mL) and saturated NaCl (5 mL)
  2. dry with materialdried (MgSO4)
  3. customevaporated at reduced pressure
  4. customgiving a yellow powder

Sources & evidence

ORD record
ord-6cd5d81d515043bab926bd34804db052
Source dataset
uspto-grants-2003_07
Patent number
US06593337B1

Reaction notes

Loading…