Dimethylmaleic anhydride → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,3-dimethylmaleinimide

HRID 231246Notes

Reaction equation

HRID 231246 reaction equation
[NH2:1][C:2]1[S:3][C:4]([C:7]([CH3:10])([CH3:9])[CH3:8])=[N:5][N:6]=1.[CH3:11][C:12]1[C:13]([O:15][C:16](=O)[C:17]=1[CH3:18])=[O:14]>C(O)(=O)C>[C:7]([C:4]1[S:3][C:2]([N:1]2[C:13](=[O:14])[C:12]([CH3:11])=[C:17]([CH3:18])[C:16]2=[O:15])=[N:6][N:5]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

4

Reactant 2

HCID 13010Dimethylmaleic anhydrideHCID 170170Buthidazolamine

Product 1

HCID 14461005N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,3-dimethylmaleinimideYield 91%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

2-Amino-5-tert-butyl-1,3,4-thiadiazole (1.57 g) and 2,3-dimethylmaleic anhydride (1.51 g) were refluxed for 5 hours in glacial acetic acid (30 ml). After the reaction, acetic acid and the excess of the 2,3-dimethylmaleic anhydride were evaporated. The residue was dissolved in dichloromethane (50 ml), and the solution was washed with a 10% aqueous solution of potassium carbonate (20 ml), and dried over anhydrous magnesium sulfate. The solvent was evaporated to give the desired N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,3-dimethylmaleinimide (2.41 g), mp. 87°-91° C.

Workup

  1. customthe excess of the 2,3-dimethylmaleic anhydride were evaporated
  2. dissolutionThe residue was dissolved in dichloromethane (50 ml)
  3. washthe solution was washed with a 10% aqueous solution of potassium carbonate (20 ml)
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-a31f1e0b1f3e4e298e59251a6d655e13
Source dataset
uspto-grants-1989_07
Patent number
US04845230

Reaction notes

Loading…