Sodium Hydroxide → 2-Cyano-6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole

HRID 2248880Notes

Reaction equation

HRID 2248880 reaction equation
[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([OH:12])[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2].Cl[CH2:14][C:15]1[CH:16]=[C:17]([CH:30]=[CH:31][CH:32]=1)[O:18][CH2:19][C:20]1[CH:29]=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=2)[N:21]=1.[OH-].[Na+]>CS(C)=O>[C:1]([C:3]1[O:4][C:5]2[CH:11]=[C:10]([O:12][CH2:14][C:15]3[CH:32]=[CH:31][CH:30]=[C:17]([O:18][CH2:19][C:20]4[CH:29]=[CH:28][C:27]5[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=5)[N:21]=4)[CH:16]=3)[CH:9]=[CH:8][C:6]=2[N:7]=1)#[N:2]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 145017062-(3-Chloromethylphenoxy)methylquinolineHCID 199947712-Cyano-6-hydroxybenzoxazole

Product 1

HCID 199947482-Cyano-6-(3-(quinolin-2-ylmethyloxy)benzyloxy)benzoxazole

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To 2-cyano-6-hydroxybenzoxazole (11.87 mmoles) and 2-((3-chloromethylphenoxy)methyl)quinoline (11.87 mmoles) in dimethylsulfoxide (20 ml) is added powdered sodium hydroxide (0.475 q). After one week the reaction mixture is poured into ice water and the resulting precipitate collected and purified by HPLC to give 2-cyano-6-(3-(quinolin-2-ylmethyloxy)benzyloxy)-benzoxazole which is used directly in the next step.

Workup

  1. customthe resulting precipitate collected
  2. custompurified by HPLC

Sources & evidence

ORD record
ord-183aa115a0a74806a443c5e9636c2d0b
Source dataset
uspto-grants-1991_08
Patent number
US05041453

Reaction notes

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