Glycol monoethyl ether → HCID 10132790, compound

HRID 2213758Notes

Reaction equation

HRID 2213758 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.[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH2:28])=[C:26]([F:31])[CH:25]=1.Cl.N1C=CC=CC=1>>[Cl:23][C:24]1[CH:30]=[CH:29][C:27]([NH:28][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)=[C:26]([F:31])[CH:25]=1

Participants

5

Reactant 4

HCID 8076Glycol monoethyl etherHCID 938984-Chloro-2-fluoroanilineHCID 10176127Pyridinium chlorideHCID 10824241HCID 10824241, compound

Product 1

HCID 10132790HCID 10132790, compoundYield 66%

Procedure

A solution of 237 mg (0.97 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile in 6 mL of 2-ethoxyethanol containing 0.15 mL (1.36 mmol) of 4-chloro-2-fluoroaniline and 112 mg of pyridine hydrochloride is heated at reflux temperature for 30 hours. The reaction mixture is cooled to room temperature and partitioned between ethyl acetate and saturated sodium bicarbonate. 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, washing with hexane to give 225 mg (66%) of an off-white solid, mp 250–251° C.

Workup

  1. temperatureat reflux temperature for 30 hours
  2. custompartitioned 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
  8. washwashing with hexane

Sources & evidence

ORD record
ord-e3818d0e9f264ef989af3fff32b95ce5
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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