p-Toluenesulfonic acid monohydrate → N-methyl-6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

HRID 36064Notes

Reaction equation

HRID 36064 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:18])([CH3:17])[CH:6]1O)=[S:4].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[C:10]2[CH:11]=[C:12]([C:15]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:18])([CH3:17])[CH:6]=1)=[S:4]

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 15054561HCID 15054561, compound

Product 1

HCID 15054568N-methyl-6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 0.44 g of N-methyl-6-cyano-3,4-dihydro-3-hydroxy-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide, 0.07 g of p-toluenesulfonic acid monohydrate, and 30 ml of toluene was heated at reflux for 10 hours. The solvent was removed by distillation, and the residue was purified by silica gel column chromatography (developing solution: CH2Cl2) to obtain 0.18 g of-N-methyl-6-cyano-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 10 hours
  3. customThe solvent was removed by distillation
  4. customthe residue was purified by silica gel column chromatography (developing solution: CH2Cl2)

Sources & evidence

ORD record
ord-5032214252f7423c99baac7bb571e4d2
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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