Hydrochloric Acid → N-methyl-6-cyano-2-ethyl-2-methyl-2H-1-benzopyran-4-carboxamide

HRID 36077Notes

Reaction equation

HRID 36077 reaction equation
[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]([CH2:18][CH3:19])([CH3:17])[CH:6]=1)=S.C1(C)C=CC(S(Cl)(=O)=[O:27])=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]#[N:16])[CH:13]=[CH:14][C:9]=2[O:8][C:7]([CH2:18][CH3:19])([CH3:17])[CH:6]=1)=[O:27]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 73974-Toluenesulfonyl chlorideHCID 15234746N-methyl-6-cyano-2-ethyl-2-methyl-2H-1-benzopyran-4-carbothioamide

Product 1

HCID 15234747N-methyl-6-cyano-2-ethyl-2-methyl-2H-1-benzopyran-4-carboxamideYield 62.2%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A mixture of 70 mg of N-methyl-6-cyano-2-ethyl-2-methyl-2H-1-benzopyran-4-carbothioamide, 55 mg of p-toluenesulfonyl chloride, and 5 ml of pyridine was heated at reflux for 6 hours. To the reaction mixture was added 2N hydrochloric acid, and the mixture was extracted with dichloromethane. The extract was dried over magnesium sulfate, and purified by silica gel column chromatography (AcOEt:n-hexane=1:1) and recrystallized from a mixture of ethyl acetate and n-hexane to obtain 41 mg of N-methyl-6-cyano-2-ethyl-2-methyl-2H-1-benzopyran-4-carboxamide represented by formula shown below.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 6 hours
  3. extractionthe mixture was extracted with dichloromethane
  4. dry with materialThe extract was dried over magnesium sulfate
  5. custompurified by silica gel column chromatography (AcOEt:n-hexane=1:1)
  6. customrecrystallized from a mixture of ethyl acetate and n-hexane

Sources & evidence

ORD record
ord-5507eb743de943129a358981cdb369bf
Source dataset
uspto-grants-1995_05
Patent number
US05412117

Reaction notes

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