Glycol monoethyl ether → HCID 9970004, compound

HRID 2213757Notes

Reaction equation

HRID 2213757 reaction equation
Cl[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[S:12][C:3]=12.C(OCCO)C.[Br:23][C:24]1[CH:25]=[C:26]([CH:28]=[CH:29][CH:30]=1)[NH2:27].Cl.N1C=CC=CC=1>>[Br:23][C:24]1[CH:25]=[C:26]([NH:27][C:2]2[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]3[C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[S:12][C:3]=23)[CH:28]=[CH:29][CH:30]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 115623-BromoanilineHCID 10176127Pyridinium chlorideHCID 10824241HCID 10824241, compound

Product 1

HCID 9970004HCID 9970004, compoundYield 58%

Procedure

A solution of 150 mg (0.61 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile in 3 mL of 2-ethoxyethanol containing 80 mg (0.74 mmol) of 3-bromoaniline and 71 mg of pyridine hydrochloride is heated at reflux temperature for 4 hours, then allowed to stir at room temperature for 3 days. The reaction mixture is partitioned between ethyl acetate and saturated sodium bicarbonate and the organic layer is dried over magnesium sulfate, filtered and concentrated in vacuo. Diethyl ether is added to the residue and the resultant solid is collected by filtration to give 139 mg (58%) of a white solid, mp 240–242° C.

Workup

  1. temperatureat reflux temperature for 4 hours
  2. customThe reaction mixture is partitioned between ethyl acetate and saturated sodium bicarbonate
  3. dry with materialthe organic layer is dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. additionDiethyl ether is added to the residue
  7. filtrationthe resultant solid is collected by filtration

Sources & evidence

ORD record
ord-420f5ea698ab45d584c36751d3bd0ae7
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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