Toluene → HCID 18350687, compound

HRID 1737268Notes

Reaction equation

HRID 1737268 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[NH:8][C:9]([C:11]1[C:12]([NH:16][C:17](=O)[CH3:18])=[CH:13][S:14][CH:15]=1)=[O:10].C1(C)C=CC=CC=1.P(Cl)(Cl)(Cl)=O>O>[CH3:18][C:17]1[N:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[C:9](=[O:10])[C:11]2[C:12](=[CH:13][S:14][CH:15]=2)[N:16]=1

Participants

5

Reactant 3

HCID 1140TolueneHCID 24813Phosphorus oxychlorideHCID 54390405HCID 54390405, compound

Product 1

HCID 18350687HCID 18350687, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-acetamidothiophene-4-carboxylic acid 2-chlorophenylamide (0.36 g, 1.23 mmol), toluene (15 mL), and phosphorous oxychloride (0.35 mL, 3.7 mmol) was refluxed 8 hours with azeotropic removal of water (Dean-Stark apparatus). The reaction was cooled and partitioned between ethyl acetate and water. 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. The residue was flash chromatographed on silica gel (20×85 mm) eluting with 10% ethyl acetate/hexane. After an unweighed forerun, 2-methyl-3-(2-chloro-phenyl)-3H-thieno[3,4-d]pyrimidin-4-one was isolated as an off white solid.

Workup

  1. temperatureThe reaction was cooled
  2. custompartitioned between ethyl acetate and water
  3. customThe phases were separated
  4. extractionthe aqueous layer was extracted with ethyl acetate
  5. washThe combined organic layer was washed with water and brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated
  8. customchromatographed on silica gel (20×85 mm)
  9. washeluting with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-96d4eb25c4f340dc9f36f0cea41a7bb5
Source dataset
uspto-grants-1999_10
Patent number
US05962457

Reaction notes

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