Acetic Acid → HCID 22414428, compound

HRID 1721335Notes

Reaction equation

HRID 1721335 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[CH2:9][CH:10]([C:13]1[S:14][CH:15]=[CH:16][C:17]=1[CH3:18])[NH:11][CH3:12].[C:19](OCC)(OCC)(OCC)[CH2:20]C.[C:31](O)(=O)C>CCOCC>[Cl:8][C:6]1[CH:5]=[CH:4][C:3]2[CH2:9][CH:10]([C:13]3[S:14][CH:15]=[CH:16][C:17]=3[CH3:18])[N:11]([CH3:31])[C:12]([CH2:19][CH3:20])=[N:1][C:2]=2[CH:7]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 66995Ethyl orthopropionateHCID 10265703HCID 10265703, compound

Product 1

HCID 22414428HCID 22414428, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A stirred solution of 3.05 g of 2-amino-4-chloro-N-methyl-α-(3-methyl-2-thienyl)benzeneethanamine, 11.63 g of triethyl orthopropionate and 3.7 ml of glacial acetic acid, was refluxed for 8 hr and then concentrated at 80° C. The residue was washed with 10% hydrochloric acid, and the aqueous phase was washed with ether, basified with 10% sodium hydroxide solution and extracted with dichloromethane. The combined organic phases were dried over anhydrous sodium sulfate, filtered and concentrated. Purification was accomplished by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, eluted with methanol, flow rate of 200 ml/min, GOW-MAC Model 80-800 UV detector). The appropriate fractions were combined and concentrated to afford a solid. The solid was dissolved in ether and filtered. The filtrate was concentrated and the residue was triturated with ether to give 1.2 g of product, mp 94°-96° C.

Workup

  1. concentrationconcentrated at 80° C
  2. washThe residue was washed with 10% hydrochloric acid
  3. washthe aqueous phase was washed with ether
  4. extractionextracted with dichloromethane
  5. dry with materialThe combined organic phases were dried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customPurification
  9. washwas accomplished by preparative HPLC (Water's Associates Prep LC/System 500A, silica gel, eluted with methanol, flow rate of 200 ml/min, GOW-MAC Model 80-800 UV detector)
  10. concentrationconcentrated
  11. customto afford a solid
  12. filtrationfiltered
  13. concentrationThe filtrate was concentrated
  14. customthe residue was triturated with ether

Sources & evidence

ORD record
ord-3d82ee92b11f4fc59927720c047ff9a4
Source dataset
uspto-grants-1996_04
Patent number
US05510346

Reaction notes

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