2-Chloroaniline → HCID 901567, compound

HRID 1737255Notes

Reaction equation

HRID 1737255 reaction equation
[CH3:1][C:2]1O[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=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>[CH3:1][C:2]1[N:15]([C:14]2[CH:16]=[CH:17][CH:18]=[CH:19][C:13]=2[Cl:12])[C:4](=[O:11])[C:5]2[S:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

4

Reactant 2

HCID 72402-ChloroanilineHCID 126692502-Methyl-thieno[3,2-d][1,3]oxazin-4-one

Product 1

HCID 901567HCID 901567, compoundYield 51.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Methyl-thieno[3,2-d][1,3]oxazin-4-one (1.67 g, 10 mmol) and o-chloroaniline (2.1 mL, 20 mmol) were combined in acetic acid (20 mL) and refluxed for 4.5 hours. The reaction was partitioned between ethyl acetate and water. The two phase mixture was treated with sodium bicarbonate until the aqueous layer was basic and the phases were then separated. The aqueous phase was extracted with ethyl acetate and the combined organic layer was washed with water and brine, dried over sodium sulfate and concentrated to leave a brown oil. This residue was purified by flash chromatography on silica gel (30×150 mm). Elution with 10% and 20% ethyl acetate/hexane gave 1.42 g (51%) of 2-methyl-3-(2-chlorophenyl)-3H-thieno[3,2-d]pyrimidin-4-one was isolated as a brown oil which solidified on standing.

Workup

  1. temperaturerefluxed for 4.5 hours
  2. customThe reaction was partitioned between ethyl acetate and water
  3. additionThe two phase mixture was treated with sodium bicarbonate until the aqueous layer
  4. customthe phases were then separated
  5. extractionThe aqueous phase was extracted with ethyl acetate
  6. washthe combined organic layer was washed with water and brine
  7. dry with materialdried over sodium sulfate
  8. concentrationconcentrated
  9. customto leave a brown oil
  10. customThis residue was purified by flash chromatography on silica gel (30×150 mm)
  11. washElution with 10% and 20% ethyl acetate/hexane

Sources & evidence

ORD record
ord-d24964b5d14144679492a6a37c961aa3
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

Loading…