Potassium Carbonate → 2-Chloro-5-(3-diethylamino-1-propoxy)nitrobenzene

HRID 8048

Reaction equation

HRID 8048 reaction equation
CS(Cl)(=O)=O.[CH2:6]([N:8]([CH2:13][CH3:14])[CH2:9][CH2:10][CH2:11][OH:12])[CH3:7].[Cl:15][C:16]1[CH:21]=[CH:20][C:19](O)=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24].C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[Cl:15][C:16]1[CH:21]=[CH:20][C:19]([O:12][CH2:11][CH2:10][CH2:9][N:8]([CH2:13][CH3:14])[CH2:6][CH3:7])=[CH:18][C:17]=1[N+:23]([O-:25])=[O:24]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 121593-(Diethylamino)-1-propanolHCID 31297Methanesulfonyl chlorideHCID 691274-Chloro-3-nitrophenol

Product 1

HCID 220147312-Chloro-5-(3-diethylamino-1-propoxy)nitrobenzeneYield 90.7%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

MsCl (6.0 mmol) was added dropwise at 0° C. to a stirred solution of 3-diethylamino-1-propanol (6.0 mmol), TEA (6.0 mmol) in anhydrous DCM (6 mL), and the mixture was stirred at the same temperature for 10 min, and at room temperature for additional 1 h. After the removal of the solvent in vacuo, the solid residue was mixed with 4-chloro-3-nitrophenol (5.0 mmol), and K2CO3 (10 mmol) in anhydrous DMF (10 mL), following the general procedure III (Step A). The crude product is purified using silica gel column chromatography 5% MeOH/DCM as eluent to yield 2-chloro-5-(3-diethylamino-1-propoxy)nitrobenzene (1.3 g).

Workup

  1. waitat room temperature for additional 1 h
  2. customAfter the removal of the solvent in vacuo
  3. customThe crude product is purified

Sources & evidence

ORD record
ord-a2ee85c640ce4339a5e720ec558b5af4
Source dataset
uspto-grants-2006_08
Patent number
US07087632B2

Linked notes

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