1,3-Benzenediamine, 5-chloro- → HCID 17950413, compound

HRID 2182612Notes

Reaction equation

HRID 2182612 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH2:9])[CH:5]=[C:6]([NH2:8])[CH:7]=1.CO[CH:12]1[CH2:16][CH2:15][CH:14](OC)O1>C(O)(=O)C>[Cl:1][C:2]1[CH:7]=[C:6]([CH:5]=[C:4]([N:9]2[CH:12]=[CH:16][CH:15]=[CH:14]2)[CH:3]=1)[NH2:8]

Participants

4

Reactant 2

HCID 733351,3-Benzenediamine, 5-chloro-HCID 790982,5-Dimethoxytetrahydrofuran

Product 1

HCID 17950413HCID 17950413, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 5-chloro-1,3-phenylenediamine (2.00 g) in acetic acid (20 mL) was added 2,5-dimethoxytetrahydrofuran (1.8 mL). After 4 hours at reflux, the reaction mixture was concentrated. The residue was suspended in satd. NaHCO3 and EtOAc. The reaction mixture was filtered and the organic layer was collected, washed with satd. NaHCO3 and brine, dried (Na2SO4), filtered and concentrated. Purification of the residue by chromatography (silica gel: EtOAc/hexane: 1/4) afforded 0.54 g of 3-chloro-5-(l-pyrrolyl) aniline. MS (m/z) 193 (MH+).

Workup

  1. temperatureAfter 4 hours at reflux
  2. concentrationthe reaction mixture was concentrated
  3. filtrationThe reaction mixture was filtered
  4. customthe organic layer was collected
  5. washwashed with satd
  6. dry with materialNaHCO3 and brine, dried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customPurification of the residue by chromatography (silica gel: EtOAc/hexane: 1/4)

Sources & evidence

ORD record
ord-abf2e7bc5bde48748636598a0ebe80b7
Source dataset
uspto-grants-2005_05
Patent number
US06897225B1

Reaction notes

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