Potassium Carbonate → 4-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)butanamide

HRID 400368Notes

Reaction equation

HRID 400368 reaction equation
[C:1]1([C:7]2[S:11][C:10]([NH2:12])=[N:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[Cl:13][CH2:14][CH2:15][CH2:16][C:17](Cl)=[O:18].C(=O)([O-])[O-].[K+].[K+]>C1(C)C=CC=CC=1>[Cl:13][CH2:14][CH2:15][CH2:16][C:17]([NH:12][C:10]1[S:11][C:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[N:8][N:9]=1)=[O:18]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 783704-Chlorobutyryl chlorideHCID 2194082-Amino-5-phenyl-1,3,4-thiadiazole

Product 1

HCID 84140754-chloro-N-(5-phenyl-1,3,4-thiadiazol-2-yl)butanamideYield 85.2%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 5-phenyl-1,3,4-thiadiazol-2-amine (7.1 g, 0.04 mol), 4-chloro-butyryl chloride (11.3 g, 9.0 ml, 0.08 mol) and potassium carbonate (5.5 g, 0.04 mole) in toluene (100 ml) was heated under reflux for 4 hr. The toluene was then evaporated under reduced pressure. The residue was then quenched with water, stirred, and filtered. The solid obtained was washed, dried and recrystallized from toluene to give the required product (9.6 g, 85% yield), mp 159-62° C., m/e 281, 87% (consistent with molecular formula C12H12ClN3OS, calcd. 281.04). 1H NMR (DMSO-d6): δ 2.07-2.10 (m, 2H, —CH2), 2.67-2.70 (m, 2H, —CH2), 3.70-3.72 (m, 2H, —CH2), 7.48-7.54 (m, 3H, ArH), 7.93-7.94 (m, 2H, ArH), 12.65 (br s, 1H, NH). 13C NMR: δ 27.9, 32.7, 45.1, 127.4, 129.8, 130.7, 131.0, 158.5, 162.4, 171.2.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 4 hr
  3. customThe toluene was then evaporated under reduced pressure
  4. customThe residue was then quenched with water
  5. filtrationfiltered
  6. customThe solid obtained
  7. washwas washed
  8. customdried
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-220eb16f95bd44ad8f5201597c5e3588
Source dataset
uspto-grants-2014_06
Patent number
US08741893B2

Reaction notes

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