p-Toluenesulfonic acid monohydrate → HCID 19037018, compound

HRID 264835Notes

Reaction equation

HRID 264835 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([CH2:22][O:23][CH3:24])[CH2:19][O:20][CH3:21].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:24][O:23][CH2:22][C:3]1([CH2:19][O:20][CH3:21])[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

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19037056HCID 19037056, compound

Product 1

HCID 19037018HCID 19037018, compoundYield 21.1%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

A mixture of 550 mg of 3,4-dihydro-3-hydroxy-2,2-bis(methoxymethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide, 0.16 g of p-toluenesulfonic acid monohydrate and 8 ml of toluene was refluxed with heating for 1.5 hours. Toluene 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 110 mg of oily 2,2-bis(methoxymethyl)-N-methyl-6-nitro-2H-1-benzopyran-4-carbothioamide.

Workup

  1. temperaturewas refluxed
  2. temperaturewith heating for 1.5 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-a657f2f3ced54c849150e8074ce1993d
Source dataset
uspto-grants-1997_07
Patent number
US05646308

Reaction notes

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