Acetic Acid → 5-(2-chlorophenyl)-1,3-dihydro-2H-thieno(2,3-e)(1,4)diazepin-2-one

HRID 262975Notes

Reaction equation

HRID 262975 reaction equation
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:4].C(O)(=O)C.CCOCC>C(O)C>[Cl:18][C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=1[C:11]1[C:10]2[CH:9]=[CH:8][S:7][C:6]=2[NH:5][C:3](=[O:4])[CH2:2][N:1]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 3283Diethyl EtherHCID 113808702-amino-N-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide

Product 1

HCID 1356185665-(2-chlorophenyl)-1,3-dihydro-2H-thieno(2,3-e)(1,4)diazepin-2-one

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

150 g (0.51 mol) of 2-aminoacetylamino-3-(o-chlorobenzoyl)-thiophene are dissolved in 2.5 liters of absolute ethanol and 250 ml of glacial acetic acid are added. The solution is heated to reflux with stirring until the reaction has ended (about 5 hours) as indicated by thin-layer chromatography (eluant: ether). The solvent is removed under a vacuum and the product taken up in 2 liters of methylene chloride. The methylene chloride solution is shaken out with dilute aqueous sodium bicarbonate solution, washed with water and evaporated. The product is brought to crystallization, treated with 150 ml of methylene chloride, refluxed and left to crystallize in a refrigerator. After filtration under a vacuum and treatment with ice-cold methylene chloride, pure 5-(o-chlorophenyl)-1,3-dihydro-2H-thieno[2,3-e]-1,4-diazepin-2-one is obtained in the form of bright-yellow crystals, melting point 221°-223° C.

Workup

  1. temperatureThe solution is heated
  2. temperatureto reflux
  3. custom(about 5 hours)
  4. customThe solvent is removed under a vacuum
  5. stirringThe methylene chloride solution is shaken out with dilute aqueous sodium bicarbonate solution
  6. washwashed with water
  7. customevaporated
  8. customThe product is brought to crystallization
  9. additiontreated with 150 ml of methylene chloride
  10. temperaturerefluxed
  11. waitleft
  12. customto crystallize in a refrigerator
  13. filtrationAfter filtration under a vacuum and treatment with ice-cold methylene chloride

Sources & evidence

ORD record
ord-5c01bf307ac0484584f702ab52e16986
Source dataset
uspto-grants-1979_05
Patent number
US04155913

Reaction notes

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