Dimethylamine → N,N-dimethyl-4-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)benzamide

HRID 647500Notes

Reaction equation

HRID 647500 reaction equation
[CH3:1][C:2]1[S:6][C:5]([S:7][CH2:8][C:9]2[CH:24]=[CH:23][C:12]([C:13]([O:15]N3C(=O)CCC3=O)=O)=[CH:11][CH:10]=2)=[N:4][N:3]=1.[CH3:25][NH:26][CH3:27].CO.CNC>CO>[CH3:25][N:26]([CH3:27])[C:13](=[O:15])[C:12]1[CH:11]=[CH:10][C:9]([CH2:8][S:7][C:5]2[S:6][C:2]([CH3:1])=[N:3][N:4]=2)=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 674DimethylamineHCID 12834422HCID 12834422, compoundHCID 22497844Dimethylamine methanol

Product 1

HCID 12834421N,N-dimethyl-4-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)benzamide

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A slurry of 3.0 grams of 1-((4-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)benzoyl)oxy)-2,5-pyrrolidinedione (0.0083 mole) was treated with 50 ml of methanol saturated with dimethylamine. After the mixture of methanol-dimethylamine went into solution, the reaction mixture was concentrated and a viscous oil obtained. Crystals formed upon drying the viscous oil in vacuo. Further purification gave the product N,N-dimethyl-4-(((5-methyl-1,3,4-thiadiazol-2-yl)thio)methyl)benzamide, confirmed by nuclear magnetic resonance, as a white solid having a melting point of 75°-80° C.

Workup

  1. concentrationthe reaction mixture was concentrated
  2. customa viscous oil obtained
  3. customCrystals formed
  4. customupon drying the viscous oil in vacuo
  5. customFurther purification

Sources & evidence

ORD record
ord-9f2dad0525bb4a0bbbfe0540e3a145a0
Source dataset
uspto-grants-1983_10
Patent number
US04409227

Reaction notes

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