Triethylamine → HCID 78319100, compound

HRID 2170833Notes

Reaction equation

HRID 2170833 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][NH:9][C:10]([C:12]2[S:13][CH:14]=[CH:15][CH:16]=2)=[O:11])=[CH:4][CH:3]=1.C(N(CC)CC)C.[C:24](N1C=CN=C1)(N1C=CN=C1)=[O:25]>C1COCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[N:9]=[C:10]([C:12]3[S:13][CH:14]=[CH:15][CH:16]=3)[O:11][C:24]2=[O:25])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 2812576HCID 2812576, compound

Product 1

HCID 78319100HCID 78319100, compoundYield 81.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of N′-(4-chlorophenyl)thiophene-2-carbohydrazide (20 g, 79.3 mmol), triethylamine (10 mL) and carbonyldiimidazole (16.2 g, 100 mmol) was refluxed in THF (100 mL) for 1 hour. The crude product obtained after the removal of the solvent was triturated with water, filtered, and dried, followed by recrystallization from ethyl acetate/hexanes to provide 3-(4-chloro-phenyl)-5-(thiophene-2-yl)-1,3,4-oxadiazol-2(3H)-one (18 g, 64.7 mmol, yield 81%). The HPLC purity of the final product was 99.9%. LC-MS [M+H] 279.9 (C12H7ClN2O2S+H, expected 279.72). The 1H-NMR spectrum was in accordance with the chemical structure.

Workup

  1. customThe crude product obtained
  2. customafter the removal of the solvent
  3. customwas triturated with water
  4. filtrationfiltered
  5. customdried
  6. customfollowed by recrystallization from ethyl acetate/hexanes

Sources & evidence

ORD record
ord-2a6e3e5dbd174f789b31e759c6e8d77d
Source dataset
uspto-grants-2015_06
Patent number
US09051309B2

Reaction notes

Loading…