Lawesson's reagent → 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide

HRID 264839Notes

Reaction equation

HRID 264839 reaction equation
[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9]([NH:11][CH3:12])=O)[C:6]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:31])=CC=1>C1C=CC=CC=1>[F:1][CH2:2][C:3]1([CH2:20][F:21])[CH:8]=[C:7]([C:9](=[S:31])[NH:11][CH3:12])[C:6]2[CH:13]=[C:14]([N+:17]([O-:19])=[O:18])[CH:15]=[CH:16][C:5]=2[O:4]1

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 190370412,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carboxamide

Product 1

HCID 104033502,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamideYield 152.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.08 g of 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carboxamide, 0.06 g of a Lawesson's reagent and 2 ml of benzene was refluxed with heating for 1 hour. The solvent was distilled. The resultant residue was purified according to silica gel column chromatography (developing solution:CH2Cl2) and further recrystallized by a mixed solvent of ethyl acetate and hexane to obtain 71 mg of 2,2-bis(fluoromethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide with a melting point of 134°-135° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 1 hour
  3. distillationThe solvent was distilled
  4. customThe resultant residue was purified
  5. customfurther recrystallized by a mixed solvent of ethyl acetate and hexane

Sources & evidence

ORD record
ord-7b3b004415fd4568826e41deb15db4e6
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

Loading…