Ethyl Acetate → 7-Hydroxy-6-methyl-8-nitro-2H-thiazolo[3,2-A]pyridin-5(3H)-one

HRID 1259416Notes

Reaction equation

HRID 1259416 reaction equation
[N+:1]([CH:4]=[C:5]1[NH:9][CH2:8][CH2:7][S:6]1)([O-:3])=[O:2].ClC1C=C(Cl)C=C(Cl)C=1[O:19][C:20](=O)[CH:21]([CH3:34])[C:22](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:23].C(OC(=O)C)C>C1(C)C(C)=CC=CC=1>[OH:23][C:22]1[C:4]([N+:1]([O-:3])=[O:2])=[C:5]2[S:6][CH2:7][CH2:8][N:9]2[C:20](=[O:19])[C:21]=1[CH3:34]

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 38355832-Nitromethylene-thiazolidineHCID 12320374Bis(2,4,6-trichlorophenyl) methylpropanedioate

Product 1

HCID 583805737-Hydroxy-6-methyl-8-nitro-2H-thiazolo[3,2-A]pyridin-5(3H)-oneYield 46.4%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-Nitromethylene-thiazolidine (7.3 g, 50 mmol) and 2-methyl-malonic acid bis-(2,4,6-trichloro-phenyl) ester (23.8 g, 50 mmol) in xylene (80 mL) was taken in a reaction flask and the flask was heated to reflux for 3 hours. The reaction mixture was monitored by TLC (100% ethylacetate). The reaction mixture was cooled, concentrated and partitioned between DCM and water. The organic layer was washed with water, brine solution, dried over Na2SO4 and concentrated. The crude product was kept at 0° C. for overnight. The solid formed was collected and washed with hexane and ether to afford 5.3 g of the product (46% yield).

Workup

  1. temperaturethe flask was heated
  2. temperatureto reflux for 3 hours
  3. temperatureThe reaction mixture was cooled
  4. concentrationconcentrated
  5. custompartitioned between DCM and water
  6. washThe organic layer was washed with water, brine solution
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated
  9. customThe solid formed
  10. customwas collected
  11. washwashed with hexane and ether

Sources & evidence

ORD record
ord-fcea8ea17e0b472eb9625d1645bb1225
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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