Toluene → HCID 19037033, compound

HRID 264830Notes

Reaction equation

HRID 264830 reaction equation
O[CH:2]1[CH:7]([C:8](=[S:11])[NH:9][CH3:10])[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4][C:3]1([CH2:20][O:21][CH3:22])[CH3:19].O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1(C)C=CC=CC=1>C(OCC)(=O)C>[CH3:22][O:21][CH2:20][C:3]1([CH3:19])[CH:2]=[C:7]([C:8](=[S:11])[NH:9][CH3:10])[C:6]2[CH:12]=[C:13]([N+:16]([O-:18])=[O:17])[CH:14]=[CH:15][C:5]=2[O:4]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 521998p-Toluenesulfonic acid monohydrateHCID 19037045HCID 19037045, compound

Product 1

HCID 19037033HCID 19037033, compoundYield 70.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 0.9 g of 3,4-dihydro-3-hydroxy-2-methoxymethyl-N,2-dimethyl-6-nitro-2H-1-benzopyran-4-carbothioamide, 0.12 g of p-toluenesulfonic acid monohydrate and 25 ml of toluene was refluxed with heating for 2 hours. Ethyl acetate was added to the mixture. After it was washed with water and dried, the solvent was distilled. The resultant residue was purified according to silica gel column chromatography (developing solution. MeOH:CH2Cl2 =1:99) to obtain 600 mg of 2-methoxymethyl-N,2-dimethyl-6-nitro-2H-1-benzopyran-4-carbothioamide with a melting point of 146°-148° C.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 2 hours
  3. washAfter it was washed with water
  4. customdried
  5. distillationthe solvent was distilled
  6. customThe resultant residue was purified

Sources & evidence

ORD record
ord-19ef3bea7c6a42d5aedb68f0c7bbef98
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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