Dimethylformamide → HCID 178432247, compound

HRID 2266470Notes

Reaction equation

HRID 2266470 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]#[N:25])=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21].[N-:26]=[N+:27]=[N-:28].[Na+].[Cl-].[NH4+].CN(C)C=O>C(OCC)(=O)C.[Cl-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:22][CH2:23][C:24]2[NH:28][N:27]=[N:26][N:25]=2)=[C:6]2[C:11]=1[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=1)=[C:7]2[CH3:21]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 68783934[8-Chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetonitrile

Product 1

HCID 178432247HCID 178432247, compound

Reagents, catalysts & solvents 2

HCID 5234Sodium ChlorideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of [8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinolin-5-yloxy]acetonitrile (0.10 g), sodium azide (0.026 g), ammonium chloride (0.022 g) and N,N-dimethylformamide (1.5 mL) was heated by microwave irradiation at 100° C. for 45 minutes. The mixture was diluted with ethyl acetate (20 mL) and saturated aqueous sodium chloride solution (20 mL). The resulting precipitate was collected by filtration, washed with water and ethyl acetate and dried to afford title compound as a white solid, 0.14 g.

Workup

  1. filtrationThe resulting precipitate was collected by filtration
  2. washwashed with water and ethyl acetate
  3. customdried

Sources & evidence

ORD record
ord-c8e45c9284534d88b5f629a2097c6561
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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