Bis(2,4,6-trichlorophenyl) propanedioate → 7-Hydroxy-8-nitro-2H-thiazolo[3,2-A]pyridin-5(3H)-one

HRID 1259434Notes

Reaction equation

HRID 1259434 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)[CH2:21][C:22](OC1C(Cl)=CC(Cl)=CC=1Cl)=[O:23]>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])[CH:21]=1

Participants

4

Reactant 2

HCID 2783450Bis(2,4,6-trichlorophenyl) propanedioateHCID 38355832-Nitromethylene-thiazolidine

Product 1

HCID 583805817-Hydroxy-8-nitro-2H-thiazolo[3,2-A]pyridin-5(3H)-oneYield 33%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

Using the same reaction conditions and workup as described for the preparation of Intermediate (I-19b), 2-nitromethylene-thiazolidine (0.65 g, 4.45 mmol) was reacted with malonic acid bis-(2,4,6-trichloro-phenyl) ester (1.5 g, 4.45 mmol) in Xylene (10 mL) to afford the crude product. Purification by column chromatography on silica gel (100% ethylacetate) afforded 0.3 g of the product (33% yield).

Workup

  1. customthe same reaction conditions and workup
  2. customto afford the crude product
  3. customPurification by column chromatography on silica gel (100% ethylacetate)

Sources & evidence

ORD record
ord-1a2ef91f54fc4a9fb26d48c5256b74e1
Source dataset
uspto-grants-2013_06
Patent number
US08466289B2

Reaction notes

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