Lawesson's reagent → N,2,2-trimethyl-6-nitro-2H-1-benzopyran-4-carbothioamide

HRID 36073Notes

Reaction equation

HRID 36073 reaction equation
[CH3:1][NH:2][C:3]([C: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])[CH:6]=1)=O.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:29])=CC=1>C1C=CC=CC=1>[CH3:1][NH:2][C:3]([C: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])[CH:6]=1)=[S:29]

Participants

4

Reactant 2

HCID 87949Lawesson's reagentHCID 15234733N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

Product 1

HCID 10423672N,2,2-trimethyl-6-nitro-2H-1-benzopyran-4-carbothioamideYield 165.1%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A mixture of 5.26 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide prepared in accordance with Example 10-(3), 4.26 g of Lawesson's reagent, and 20 ml of benzene was heated at reflux for 1.5 hours. The reaction mixture was concentrated under reduced pressure, and the residue was subjected to silica gel column chromato- graphy (developing solution: methylene chloride) and then recrystallized from a mixture of ethyl acetate and n-hexane to obtain 4.84 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated under reduced pressure
  4. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-2c2ed58775af4217998beb3c9b12a545
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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