2-Chloroaniline → HCID 54390405, compound

HRID 430522Notes

Reaction equation

HRID 430522 reaction equation
[CH3:1][C:2]1[O:3][C:4](=[O:11])[C:5]2[C:6](=[CH:8][S:9][CH:10]=2)[N:7]=1.[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH2:15]>C(O)(=O)C>[Cl:12][C:13]1[CH:19]=[CH:18][CH:17]=[CH:16][C:14]=1[NH:15][C:4]([C:5]1[C:6]([NH:7][C:2](=[O:3])[CH3:1])=[CH:8][S:9][CH:10]=1)=[O:11]

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 15425486HCID 15425486, compound

Product 1

HCID 54390405HCID 54390405, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a slurry of 2-methyl-thieno[3,4-d][1,3]oxazin-4-one (1.3 g, 7.78 mmol) and acetic acid (15 mL) was added 2-chloroaniline (1.64 mL, 15.57 mmol). The mixture was refluxed 4 hours, cooled, and concentrated. The residue was partitioned between ethyl acetate and water and the aqueous phase was made basic by careful addition of saturated aqueous sodium bicarbonate. The phases were separated and the aqueous layer was extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated to a black oil. The oil was flash chromatographed on silica gel (30×100 mm) eluting with 10% ethyl acetate/hexane. The first component eluting from the column, 0.363 g of white solid was identified as 3-acetamidothiophene-4-carboxylic acid 2-chlorophenylamide.

Workup

  1. temperatureThe mixture was refluxed 4 hours
  2. temperaturecooled
  3. concentrationconcentrated
  4. customThe residue was partitioned between ethyl acetate and water
  5. additionthe aqueous phase was made basic by careful addition of saturated aqueous sodium bicarbonate
  6. customThe phases were separated
  7. extractionthe aqueous layer was extracted with ethyl acetate
  8. washThe combined organic layer was washed with water and brine
  9. dry with materialdried over sodium sulfate
  10. concentrationconcentrated to a black oil
  11. customchromatographed on silica gel (30×100 mm)
  12. washeluting with 10% ethyl acetate/hexane
  13. washThe first component eluting from the column, 0.363 g of white solid

Sources & evidence

ORD record
ord-5e63ab49db9c4db7958fa75274d4a671
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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