4-Toluenesulfonyl chloride → N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

HRID 36072Notes

Reaction equation

HRID 36072 reaction equation
[CH3:1][NH:2][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])[CH:6]1O)=S.C1(C)C=CC(S(Cl)(=O)=[O:28])=CC=1>N1C=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)=[O:28]

Participants

4

Reactant 2

HCID 73974-Toluenesulfonyl chlorideHCID 15234732N,2,2-trimethyl-3,4-dihydro-3-hydroxy-6-nitro-2H-1-benzopyran-4-carbothioamide

Product 1

HCID 15234733N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamideYield 67.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.42 g of N-methyl-6-nitro-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide, 0.58 g of p-toluenesulfonyl chloride, and 30 ml of pyridine was heated under reflux for 3 hours. The reaction mixture was concentrated, and 2N hydrochloric acid was added to the residue. The mixture was extracted with dichloromethane, and the extract was dried over magnesium sulfate. The residue was purified by silica gel column chromatography (CH2Cl2) and then recrystalllzed from ethyl acetate to obtain 0.25 g of N-methyl-6-nitro-2,2-dimethyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 3 hours
  3. concentrationThe reaction mixture was concentrated
  4. addition2N hydrochloric acid was added to the residue
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialthe extract was dried over magnesium sulfate
  7. customThe residue was purified by silica gel column chromatography (CH2Cl2)

Sources & evidence

ORD record
ord-3864c1248583427f9062f0f912de4106
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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