Water → HCID 85524395, compound

HRID 1773047Notes

Reaction equation

HRID 1773047 reaction equation
[CH:1]1[C:14]2[NH:13][C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[S:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21]Br.[OH-].[Na+].O>CN(C)C=O.C(Cl)(Cl)Cl>[Br:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][N:13]1[C:14]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[S:6][C:7]2[C:12]1=[CH:11][CH:10]=[CH:9][CH:8]=2

Participants

7

Reactant 4

HCID 962WaterHCID 7108PhenothiazineHCID 123681,6-DibromohexaneHCID 14798Sodium Hydroxide

Product 1

HCID 85524395HCID 85524395, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent

Procedure

Phenothiazine (5.0 g, 0.025 mol) and 1,6-dibromohexane (10.0 g, 0.065 mol) were dissolved in 100 mL of DMF (dimethyl formamide), and NaOH (sodium hydride, 0.98 g, 0.041 mol) was slowly added at room temperature. The resulting mixture was stirred at room temperature for 8 hr. After completion of the reaction, work-up was implemented in a solvent mixture of water and CHCl3 at 1:1. Thereafter, the organic layer was separated using an extraction method, and the solvent was removed under reduced pressure, followed by silica gel column chromatography (chloroform:hexane, 1:5), affording a transparent liquid product (4.5 g, 49.7%).

Workup

  1. customAfter completion of the reaction
  2. customThereafter, the organic layer was separated
  3. extractionan extraction method
  4. customthe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-8f881173fd954a05b1fea09d54d3be8b
Source dataset
uspto-grants-2016_02
Patent number
US09251964B2

Reaction notes

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