Benzene → HCID 21831322, compound

HRID 363455Notes

Reaction equation

HRID 363455 reaction equation
[F:1][CH2:2][C:3]1([CH2:23][F:24])[CH:8]=[C:7]([N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=O)[C:6]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:5]=2[O:4]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:34])=CC=1.C1C=CC=CC=1>ClCCCl>[F:1][CH2:2][C:3]1([CH2:23][F:24])[CH:8]=[C:7]([N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[S:34])[C:6]2[CH:16]=[C:17]([N+:20]([O-:22])=[O:21])[CH:18]=[CH:19][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 241BenzeneHCID 87949Lawesson's reagentHCID 21831314HCID 21831314, compound

Product 1

HCID 21831322HCID 21831322, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A mixture of 0.13 g of 2,2-bisfluoromethyl-6-nitro-4-(1,2-dihydro-2-oxo-1-pyridyl)-2H-1-benzopyran, 83 mg of a Lawesson's reagent, 1 ml of benzene and 1 ml of 1,2-dichloroethane was refluxed for 3 hours and the solvent was distilled off. The resultant residue was purified using silica gel column chromatography (developing solution, CH2Cl2), and then, recrystallized from a mixture of ethyl acetate and hexane to obtain 0.05 g of 2,2-bisfluoromethyl-6-nitro-4-(1,2-dihydro-2-thioxo-1-pyridyl)-2H-1-benzopyran represented by the following formula having a melting point of 209°-210° C.

Workup

  1. temperaturewas refluxed for 3 hours
  2. distillationthe solvent was distilled off
  3. customThe resultant residue was purified
  4. customrecrystallized from a mixture of ethyl acetate and hexane

Sources & evidence

ORD record
ord-b2bd58d0a45144a0a2881de30edadfe5
Source dataset
uspto-grants-1999_02
Patent number
US05874446

Reaction notes

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