Ethylenediaminetetraacetic Acid → HCID 22144541, compound

HRID 858249Notes

Reaction equation

HRID 858249 reaction equation
Br[C:2]1[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=[C:4]([O:19][CH3:20])[CH:3]=1.[Cu][C:22]#[N:23].C(N(CC(O)=O)CC(O)=O)CN(CC(O)=O)CC(O)=O>CN(C)C=O>[CH3:20][O:19][C:4]1[CH:3]=[C:2]([C:22]#[N:23])[C:10]2[O:9][C:8]([C:11]3[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=3)=[N:7][C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6049Ethylenediaminetetraacetic AcidHCID 121489697-Bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazoleHCID 178418546HCID 178418546, compound

Product 1

HCID 22144541HCID 22144541, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 7-bromo-5-methoxy-2-(4-methoxyphenyl)-1,3-benzoxazole (200 mg, 0.60 mmol), in anhydrous N,N dimethylformamide (135 mL) was stirred and heated to reflux under dry nitrogen with copper(I) cyanide (80 mg, 0.90 mmol) for 4 h. The mixture was cooled and poured into an excess of aqueous ethylenediaminetetraacetic acid. Isolation of the crude product gave the nitrile (164 mg, 98% yield) as tan needles from (30% EtOAc/petroleum ether); m.p. 180–183° C.; MS m/e 281 (M+H)+.

Workup

  1. temperatureheated
  2. temperatureThe mixture was cooled

Sources & evidence

ORD record
ord-d38cd9c6658349fe9456c4d24f691ab9
Source dataset
uspto-grants-2006_12
Patent number
US07148247B2

Reaction notes

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