Hydrochloric Acid → HCID 19360262, compound

HRID 1728623Notes

Reaction equation

HRID 1728623 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([NH:10][C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:8][S:7][C:6]=2[CH:17]=1.[H-].[Na+].Br[CH:21]([CH3:23])[CH3:22].Cl>CN(C)C=O.C(#N)C>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[C:9]([N:10]([CH:21]([CH3:23])[CH3:22])[C:11]3[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=3)=[CH:8][S:7][C:6]=2[CH:17]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 63582-BromopropaneHCID 24758Sodium hydride2×HCID 19360159HCID 19360159, compound

Product 1

HCID 19360262HCID 19360262, compoundYield 76.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent2×HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

A solution of 6-chloro-3-(4-pyridinylamino)benzo[b]thiophene (2.43 g, 9.3 mmole) in 20 mL of dimethylformamide was added to a suspension of NaH (0.48 g of 60% in oil, 12.1 mmole) in DMF. To this was added 2-bromopropane (1.26 g, 10.2 mmole) and the reaction mixture was heated to 50° C. During the next 5 hours, an additional 200 mg of NaH and 1 g of the bromo compound were added three separate times. The reaction mixture was then quenched into water and extracted with ethyl acetate (3×). The combined organics were washed with water (3×), dried (MgSO4), filtered and concentrated. Purification of the residue via flash chromatography (C6H5CH3 →5%Et3N/C6H5CH3) gave 1.57 of an oil. This was dissolved in acetonitrile, treated with ethereal HCl and the salt was crystallized out with additional ether to give 1.20 g of a yellowish powder, mp: 244°-246° C.

Workup

  1. customseparate times
  2. customThe reaction mixture was then quenched into water
  3. extractionextracted with ethyl acetate (3×)
  4. washThe combined organics were washed with water (3×)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification of the residue via flash chromatography (C6H5CH3 →5%Et3N/C6H5CH3)
  9. customgave 1.57 of an oil
  10. customthe salt was crystallized out with additional ether

Sources & evidence

ORD record
ord-e29c954764ea4f18b3999e1306a9e582
Source dataset
uspto-grants-1994_07
Patent number
US05328920

Reaction notes

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