Toluene → N-(5-ethyl-1,3,4-thiadiazol-2-yl)butanamide

HRID 2256201

Reaction equation

HRID 2256201 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:7][CH3:8])=[N:5][N:6]=1.C1(C)C=CC=CC=1.[C:16](Cl)(=[O:20])[CH2:17][CH2:18][CH3:19].C(=O)(O)[O-].[Na+]>C(OCC)(=O)C.C(N(CC)CC)C>[C:16]([NH:1][C:2]1[S:3][C:4]([CH2:7][CH3:8])=[N:5][N:6]=1)(=[O:20])[CH2:17][CH2:18][CH3:19]

Participants

7

Reactant 4

HCID 1140TolueneHCID 8855Butyryl chlorideHCID 264442-Amino-5-ethyl-1,3,4-thiadiazoleHCID 516892Sodium Bicarbonate

Product 1

HCID 693955N-(5-ethyl-1,3,4-thiadiazol-2-yl)butanamideYield 80.4%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineSolventHCID 8857Ethyl AcetateSolvent

Procedure

2-Amino-5-ethyl-1,3,4-thiadiazole (0.5 g) was added to a mixture of toluene (5 ml) and triethylamine (0.4 g). With stirring, butyryl chloride (0.5 g) was added to the suspension at room temperature. After stirring for 2 hours, aqueous sodium bicarbonate solution and ethyl acetate were added to the reaction mixture. The organic layer was separated and washed with water several times. The precipitated crystals and the organic layer were combined and the solvent was concentrated to 5 ml. The precipitated crystals were filtrated and dried. The title compound (0.62 g) was obtained.

Workup

  1. stirringAfter stirring for 2 hours
  2. customThe organic layer was separated
  3. washwashed with water several times
  4. concentrationthe solvent was concentrated to 5 ml
  5. filtrationThe precipitated crystals were filtrated
  6. customdried

Sources & evidence

ORD record
ord-3677fff9712043b1a5b3ea709ac8e1e9
Source dataset
uspto-grants-1997_08
Patent number
US05654322

Linked notes

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