Lawesson's reagent → HCID 19939971, compound

HRID 36082Notes

Reaction equation

HRID 36082 reaction equation
[CH3:1][N:2]([CH3:20])[C:3]([CH:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:19])([CH3:18])[CH2:6]1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:30])=CC=1>C1C=CC=CC=1>[CH3:1][N:2]([CH3:20])[C:3]([CH:5]1[C:10]2[CH:11]=[C:12]([N+:15]([O-:17])=[O:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:19])([CH3:18])[CH2:6]1)=[S:30]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 15234760HCID 15234760, compound

Product 1

HCID 19939971HCID 19939971, compoundYield 137.4%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.43 g of N,N-dimethyl-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide, 0.33 g of Lawesson's reagent, and 2 ml of benzene was heated under reflux for 30 minutes. The reaction product was purified by silica gel column chromatography (CH2Cl2) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 0.33 g of N,N-dimethyl-3,4-dihydro-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 30 minutes
  3. customThe reaction product was purified by silica gel column chromatography (CH2Cl2)
  4. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-e7cffa7ce1bd4e769e67ca089684ac87
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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