2,4-Dichloroaniline → HCID 10591320, compound

HRID 2213759Notes

Reaction equation

HRID 2213759 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]=CC=3S[C:3]=12.[Cl:17][C:18]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=1[NH2:20].Cl.N1C=CC=CC=1>CO>[Cl:17][C:18]1[CH:24]=[C:23]([Cl:25])[CH:22]=[CH:21][C:19]=1[NH:20][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]2[CH:10]=[CH:16][CH:15]=[CH:14][C:3]=12

Participants

5

Reactant 3

HCID 111232,4-DichloroanilineHCID 10176127Pyridinium chlorideHCID 10824241HCID 10824241, compound2×

Product 1

HCID 10591320HCID 10591320, compoundYield 70.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 250 mg (1.02 mmol) of 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile, 530 mg (3.27 mmol) of 2,4-dichloroaniline and 112 mg of pyridine hydrochloride is heated until no 4-chlorobenzo[4,5]thieno[3,2-b]pyridine-3-carbonitrile remained as measured by thin layer chromatography. The reaction mire is cooled to room temperature and the solid is treated with methanol and then 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 solid is collected by filtration to give 225 mg (66%) of a yellow solid. An analytical sample is obtained by column chromatography, eluting with 6:1 hexane/ethyl acetate, to provide a fight yellow solid, mp 260–262° C.

Workup

  1. custompartitioned between ethyl acetate and saturated sodium bicarbonate
  2. dry with materialThe organic layer is dried over magnesium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo
  5. additionDiethyl ether is added to the residue
  6. filtrationthe solid is collected by filtration

Sources & evidence

ORD record
ord-f443570f222b4c12b359b956f9974db0
Source dataset
uspto-grants-2006_09
Patent number
US07105531B2

Reaction notes

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