Water → HCID 11484354, compound

HRID 929494Notes

Reaction equation

HRID 929494 reaction equation
Br[CH2:2]/[C:3](/[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)=[C:4](/[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)\[CH2:5]Br.[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.O>C(Cl)Cl>[Cl:19][C:20]1[CH:26]=[CH:25][C:23]([N:24]2[CH2:5][C:4]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:3]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[CH2:2]2)=[CH:22][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 78124-ChloroanilineHCID 13442492HCID 13442492, compound

Product 1

HCID 11484354HCID 11484354, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

After dissolving compound 20 (300 mg, 0.819 mmol) and 4-chloroaniline (105 mg, 0.819 mmol) in DCM (10 ml), TEA (457 l, 3.28 mmol) was added thereto and the reflux was conducted for 4 hours. After the termination of the reaction, the temperature was reduced to room temperature and water was added thereto. The organic layer was washed with water and water was removed by using anhydrous Na2SO4. After the distillation under the reduced pressure was carried out for the removal of the solvent, column chromatography was conducted to obtain compound 21.

Workup

  1. additionwas added
  2. customAfter the termination of the reaction
  3. customwas reduced to room temperature
  4. washThe organic layer was washed with water and water
  5. customwas removed
  6. distillationAfter the distillation under the reduced pressure
  7. customwas carried out for the removal of the solvent, column chromatography

Sources & evidence

ORD record
ord-531d793d76434ef880af794e479fb505
Source dataset
uspto-grants-2016_03
Patent number
US09296690B2

Reaction notes

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