Water → HCID 44360668, compound

HRID 1779493Notes

Reaction equation

HRID 1779493 reaction equation
O.Cl.Cl[CH2:4][CH2:5][N:6]([CH3:8])[CH3:7].[Cl:9][C:10]1[CH:18]=[CH:17][C:16]2[N:15]3[CH:19]=[CH:20][CH:21]=[C:14]3[C:13](=[N:22][OH:23])[C:12]=2[CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>CC(C)=O>[Cl:9][C:10]1[CH:18]=[CH:17][C:16]2[N:15]3[CH:19]=[CH:20][CH:21]=[C:14]3[C:13](=[N:22][O:23][CH2:4][CH2:5][N:6]([CH3:8])[CH3:7])[C:12]=2[CH:11]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11636816N,N-Dimethylaminoethyl chloride hydrochlorideHCID 73677881HCID 73677881, compound

Product 1

HCID 44360668HCID 44360668, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Add 5 ml of water, 0.94 g (6.5 mmol) of 1-chloro-2-(N,N-dimethylamino)ethane hydrochloride and 1.19 g (5.44 mmol) of 7-chloro-9-hydroxyiminopyrrolo[1,2-a]indole (Preparation 46) in succession to a solution of 1.56 g (14.7 mmol) of sodium carbonate in 100 ml of acetone, then heat the reaction mixture at reflux for 36 hours. The acetone is removed under reduced pressure and the residue is taken up in 50 ml of water and extracted with diethyl ether. The ethereal phase is washed with water, dried over magnesium sulfate, rendered colourless with animal charcoal, and then concentrated to dryness to yield the title product in the form of an oil (base).

Workup

  1. temperatureheat the reaction mixture
  2. temperatureat reflux for 36 hours
  3. customThe acetone is removed under reduced pressure
  4. extractionextracted with diethyl ether
  5. washThe ethereal phase is washed with water
  6. dry with materialdried over magnesium sulfate
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-9543a6687d6d44ef99fee5f3dc66e1b1
Source dataset
uspto-grants-1997_05
Patent number
US05627203

Reaction notes

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