Toluene → HCID 178432246, compound

HRID 2266529Notes

Reaction equation

HRID 2266529 reaction equation
[Cl:1][C:2]1[C:11]2[N:10]=[C:9]([CH3:12])[C:8]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)=[C:7]([CH3:21])[C:6]=2[C:5]([C:22]#[N:23])=[CH:4][CH:3]=1.C1(C)C=CC=CC=1.C[Si]([N:35]=[N+:36]=[N-:37])(C)C.C([Sn](=O)CCCC)CCC>C(OCC)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:22]2[NH:37][N:36]=[N:35][N:23]=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

6

Reactant 4

HCID 1140TolueneHCID 61221Dibutyltin oxideHCID 78378AzidotrimethylsilaneHCID 68782476HCID 68782476, compound

Product 1

HCID 178432246HCID 178432246, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 8-chloro-3-(4-chlorobenzyl)-2,4-dimethylquinoline-5-carbonitrile (0.048 g), toluene (1.5 mL), trimethylsilyl azide (0.081 g) and dibutyltin oxide (0.007 g) were sealed in a flask and heated at 100° C. for 66 hours. The mixture was cooled to room temperature and diluted with ethyl acetate. The resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution and the pH of the aqueous phase was adjusted to 5 by the addition of glacial acetic acid. The resulting precipitate was collected by filtration, washed with diluted aqueous acetic acid solution and dried to afford title compound as a white solid, 0.017 g.

Workup

  1. customwere sealed in a flask
  2. temperatureThe mixture was cooled to room temperature
  3. washThe resulting mixture was washed with saturated aqueous sodium hydrogen carbonate solution
  4. additionthe pH of the aqueous phase was adjusted to 5 by the addition of glacial acetic acid
  5. filtrationThe resulting precipitate was collected by filtration
  6. washwashed with diluted aqueous acetic acid solution
  7. customdried

Sources & evidence

ORD record
ord-b5153cb35e5b4726aed26342daa0173d
Source dataset
uspto-grants-2010_12
Patent number
US07858640B2

Reaction notes

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