Lawesson's reagent → HCID 19939975, compound

HRID 36069Notes

Reaction equation

HRID 36069 reaction equation
[CH2:1]([NH:3][C:4]([C:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[CH:7]=1)=O)[CH3:2].COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1C=CC=CC=1>[CH2:1]([NH:3][C:4]([C:6]1[C:11]2[CH:12]=[C:13]([C:16]#[N:17])[CH:14]=[CH:15][C:10]=2[O:9][C:8]([CH3:19])([CH3:18])[CH:7]=1)=[S:29])[CH3:2]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 19939965HCID 19939965, compound

Product 1

HCID 19939975HCID 19939975, compoundYield 80.7%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 0.14 g of N-ethyl-6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carbamide, 3.45 g of Lawesson's reagent, and 10 ml of benzene was refluxed for 1 hour. Any insoluble matter was collected by filtration with suction and washed with methylene chloride. The mother liquor and the washing were combined, and the solvent was removed therefrom by distillation. The residue was purified by silica gel column chromatography (developing solution: CH2Cl2) to obtain 0.12 g of N-ethyl-6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

Workup

  1. temperaturewas refluxed for 1 hour
  2. filtrationAny insoluble matter was collected by filtration with suction
  3. washwashed with methylene chloride
  4. customthe solvent was removed
  5. distillationby distillation
  6. customThe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

Sources & evidence

ORD record
ord-2eeee1cbbc6c405f9ed7f2914acc4a1b
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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