Toluene → N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide

HRID 264844Notes

Reaction equation

HRID 264844 reaction equation
O[CH:2]1[C:7]2([CH2:12][CH2:11][O:10][CH2:9][CH2:8]2)[O:6][C:5]2[CH:13]=[CH:14][C:15]([N+:17]([O-:19])=[O:18])=[CH:16][C:4]=2[CH:3]1[C:20](=[S:23])[NH:21][CH3:22].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>O>[CH3:22][NH:21][C:20]([C:3]1[C:4]2[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:5]=2[O:6][C:7]2([CH2:8][CH2:9][O:10][CH2:11][CH2:12]2)[CH:2]=1)=[S:23]

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 190370263,4-dihydro-3-hydroxy-N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide

Product 1

HCID 19037011N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamideYield 59.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.66 g of 3,4-dihydro-3-hydroxy-N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide, 1.0 g of p-toluenesulfonic acid monohydrate and 100 ml of toluene was refluxed with heating for 1.5 hours. Water was added therein and the mixture was extracted with methylene chloride. An organic layer was washed and dried, and the solvent was distilled. The obtained residue was purified according to silica gel column chromatography (developing solution, MeOH:CH2Cl2 =1:99) to obtain 0.93 g of N-methyl-6-nitrospiro[2H-1-benzopyran-2,4'-tetrahydropyran]-4-carbothioamide with a melting point of 223°-225° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 1.5 hours
  3. extractionthe mixture was extracted with methylene chloride
  4. washAn organic layer was washed
  5. customdried
  6. distillationthe solvent was distilled
  7. customThe obtained residue was purified

Sources & evidence

ORD record
ord-34e83e75e9d94623b6a5348b1657f7a6
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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