Methanol → N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole

HRID 1761804Notes

Reaction equation

HRID 1761804 reaction equation
[BH4-].[Na+].CO.[C:5]([C:9]1[S:13][C:12]([N:14]2[C:18](=[O:19])[C:17]([CH3:20])=[C:16]([CH3:21])[C:15]2=[O:22])=[N:11][N:10]=1)([CH3:8])([CH3:7])[CH3:6]>C(O)(=O)C>[C:5]([C:9]1[S:13][C:12]([N:14]2[C:15](=[O:22])[C:16]([CH3:21])=[C:17]([CH3:20])[CH:18]2[OH:19])=[N:11][N:10]=1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 4311764Sodium borohydrideHCID 14461005N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,3-dimethylmaleinimide

Product 1

HCID 14461006N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrroleYield 77.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

Sodium borohydride (0.07 g) was added at room temperature to a methanol solution (100 ml) of N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-2,3-dimethylmaleinimide (0.95 g), and the mixture was stirred for 3 hours. After the reaction, glacial acetic acid (0.5 ml) was added and the solvent was evaporated under reduced pressure. Water (30 ml) was added to the residue, and potassium carbonate was added to make the mixture alkaline. It was extracted with dichloromethane (50 ml×2). The extractants were dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The resulting crude crystals were washed with a small amount of diethyl ether to give the desired N-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3,4-dimethyl-2-hydroxy-5-oxo-2,5-dihydropyrrole (0.74 g). mp. 179°-182° C.

Workup

  1. additionwas added
  2. customthe solvent was evaporated under reduced pressure
  3. additionWater (30 ml) was added to the residue, and potassium carbonate
  4. additionwas added
  5. extractionIt was extracted with dichloromethane (50 ml×2)
  6. dry with materialThe extractants were dried over anhydrous magnesium sulfate
  7. customthe solvent was evaporated under reduced pressure
  8. washThe resulting crude crystals were washed with a small amount of diethyl ether

Sources & evidence

ORD record
ord-4b26b4b4d69f45c19615b626708641dc
Source dataset
uspto-grants-1989_05
Patent number
US04828604

Reaction notes

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