Pyridine → [3-[3-Methyl(1,2,4-oxadiazol-5-yl)]phenyl]carbamic acid, 4-nitrophenyl ester

HRID 1492453Notes

Reaction equation

HRID 1492453 reaction equation
[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([NH2:13])[CH:10]=[CH:11][CH:12]=2)[O:4][N:3]=1.N1C=CC=CC=1.Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([N+:30]([O-:32])=[O:31])=[CH:26][CH:25]=1)=[O:22]>C(#N)C>[CH3:1][C:2]1[N:6]=[C:5]([C:7]2[CH:8]=[C:9]([NH:13][C:21](=[O:22])[O:23][C:24]3[CH:25]=[CH:26][C:27]([N+:30]([O-:32])=[O:31])=[CH:28][CH:29]=3)[CH:10]=[CH:11][CH:12]=2)[O:4][N:3]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 821294-Nitrophenyl chloroformateHCID 126766813-(3-Methyl-1,2,4-oxadiazol-5-yl)aniline

Product 1

HCID 57105596[3-[3-Methyl(1,2,4-oxadiazol-5-yl)]phenyl]carbamic acid, 4-nitrophenyl esterYield 82%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A solution of 3-[3-methyl(1,2,4-oxadiazol-5-yl)]phenyl amine (1.00 g, 5.7 mmol, prepared in sequence by the procedures described by Lin et al., J. Org. Chem., 1979, 44, 4160 and Bellamy and Ou, Tetrahedron Letters, 1984, 25, 839) in acetonitrile (25 mL) and pyridine (0.46 mL, 0.45 g, 5.7 mmol) under argon at 0° C. was treated with p-nitrophenyl chloroformate ( 1.15 g, 5.7 mmol) and was stirred at room temperature overnight. The reaction mixture was concentrated in vacuo and an effort was made to partition the remaining oil between ethyl acetate and 10% citric acid, resulting in separation of a solid insoluble in either phase. The solid was collected, triturated with hexane and dried in vacuo to yield 1.59 g (82%) of the title compound, m.p. 217°-220° C. TLC, silica gel, EtOAc/MeOH/HOAc (20:1:.2), Rf =0.75; M.S. (M+H)+ at 341, M.W. 340. This material contained minor impurities and was used without further purification.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customto partition the remaining oil between ethyl acetate and 10% citric acid
  3. customresulting in separation of a solid insoluble in either phase
  4. customThe solid was collected
  5. customtriturated with hexane
  6. customdried in vacuo

Sources & evidence

ORD record
ord-a91ae972b21543539ee6b59cc8596135
Source dataset
uspto-grants-1994_12
Patent number
US05374643

Reaction notes

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