Triethylamine → 5-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamide

HRID 1741153Notes

Reaction equation

HRID 1741153 reaction equation
[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]([NH:13][NH2:14])=[O:12].C(N(CC)CC)C.C1C=CC(O[C:29](OC2C=CC=CC=2)=[N:30][C:31]#[N:32])=CC=1>C(O)(C)C>[CH:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][C:2]=1[C:11]1[O:12][CH:29]([NH:30][C:31]#[N:32])[NH:14][N:13]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 1234852-NaphthohydrazideHCID 688090Diphenyl N-Cyanocarbonimidate

Product 1

HCID 187074915-Naphthalen-2-yl-2,3-dihydro-[1,3,4]oxadiazol-2-yl-cyanamideYield 51%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a stirred solution of naphthalene-2-carboxylic acid hydrazide (0.7 g, 3.76 mmol) in isopropanol (40 ml) was added triethylamine (630 μl, 4.51 mmol) and diphenyl cyanocarbonimidate (0.99 g, 4.14 mmol) and the resulting reaction mixture was stirred at room temperature for 1.5 h. The volatiles were evaporated in vacuo and to the residue was added water (50 ml) and diethyl ether (50 ml). The organic phase was separated and the aqueous phase was acidified to pH=1 with concentrated hydrochloric acid. The precipitate was filtered off and washed with water (3×10 ml) and diethyl ether (2×10 ml) and dried in vacuo at 50° C. which afforded 0.45 g (51%) of the title compound as a solid.

Workup

  1. customthe resulting reaction mixture
  2. customThe volatiles were evaporated in vacuo and to the residue
  3. additionwas added water (50 ml) and diethyl ether (50 ml)
  4. customThe organic phase was separated
  5. filtrationThe precipitate was filtered off
  6. washwashed with water (3×10 ml) and diethyl ether (2×10 ml)
  7. customdried in vacuo at 50° C. which

Sources & evidence

ORD record
ord-8fbc85e9112c436ab5556959bf864942
Source dataset
uspto-grants-1999_10
Patent number
US05972978

Reaction notes

Loading…