Hydrochloric Acid → N-methyl-6-trifluoromethyl-2,2-dimethyl-2H-1-benzopyran-4-carboxamide

HRID 36076Notes

Reaction equation

HRID 36076 reaction equation
[CH3:1][NH:2][C:3]([CH:5]1[C:10]2[CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:20])([CH3:19])[CH:6]1O)=S.C1(C)C=CC(S(Cl)(=O)=[O:29])=CC=1.Cl>N1C=CC=CC=1>[CH3:1][NH:2][C:3]([C:5]1[C:10]2[CH:11]=[C:12]([C:15]([F:18])([F:17])[F:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH3:20])([CH3:19])[CH:6]=1)=[O:29]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15234745N-methyl-3,4-dihydro-3-hydroxy-6-trifluoromethyl-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide

Product 1

HCID 15234735N-methyl-6-trifluoromethyl-2,2-dimethyl-2H-1-benzopyran-4-carboxamideYield 29%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 0.17 g of N-methyl-3,4-dihydro-3-hydroxy-6-trifluoromethyl-2,2-dimethyl-2H-1-benzopyran-4-carbothioamide, 0.21 g of p-toluenesulfonyl chloride, and 10 ml of pyridine was heated at reflux for 4 hours. To the reaction mixture was added 2N hydrochloric acid, and the mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate. The residue was purified by silica gel column chromatography (CH2Cl2 :methanol=100:1) and then recrystallized from a mixture of diethyl ether and n-hexane to obtain 44 mg of N-methyl-6-trifluoromethyl-2,2-dimethyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over magnesium sulfate
  5. customThe residue was purified by silica gel column chromatography (CH2Cl2 :methanol=100:1)
  6. customrecrystallized from a mixture of diethyl ether and n-hexane

Sources & evidence

ORD record
ord-61098e255c774fa1af4cb299f247a733
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

Loading…