Triethylamine → 5-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazol-2-yl-cyanamide

HRID 2211187Notes

Reaction equation

HRID 2211187 reaction equation
[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]([NH:15][NH2:16])=[O:14].C(N(CC)CC)C.C1C=CC(O[C:35](OC2C=CC=CC=2)=[N:36][C:37]#[N:38])=CC=1>CC(O)C>[Cl:1][C:2]1[C:7]([CH3:8])=[CH:6][CH:5]=[C:4]([Cl:9])[C:3]=1[NH:10][C:11]1[CH:20]=[CH:19][CH:18]=[CH:17][C:12]=1[C:13]1[O:14][C:35]([NH:36][C:37]#[N:38])=[N:16][N:15]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 688090Diphenyl N-CyanocarbonimidateHCID 14951339HCID 14951339, compound

Product 1

HCID 149513715-[2-(2,6-Dichloro-3-methyl-phenylamino)-phenyl]-[1,3,4]oxadiazol-2-yl-cyanamideYield 22%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

To a suspension of 2-[(2,6-dichloro-3-methylphenyl)amino]-benzoic acid hydrazide (394.1 mg, 1.27 mmoles) in 20 ml of 2-propanol is added triethylamine (200 μl, 1.43 mmoles) followed by diphenyl cyanocarbonimidate (371.9 mg, 1.56 mmoles). After 1.5 hours the resultant yellow solution is concentrated in vacuo. The residue is dissolved in 10 ml of ethyl acetate and partitioned between water and a 1:1 mixture of ether and hexane. The aqueous layer is acidified with 1N hydrochloric acid, and the resultant white solid is collected by filtration to provide 99.3 mg (22%) of 5-[2-[(2,6-dichloro-3-methylphenyl)amino]phenyl]-1,3,4-oxadiazol-2-yl-cyanamide, mp above 215° C.

Workup

  1. concentrationAfter 1.5 hours the resultant yellow solution is concentrated in vacuo
  2. dissolutionThe residue is dissolved in 10 ml of ethyl acetate
  3. custompartitioned between water
  4. additiona 1:1 mixture of ether and hexane
  5. filtrationthe resultant white solid is collected by filtration

Sources & evidence

ORD record
ord-4d1e36a0911947c0bfdaf76e58fd4953
Source dataset
uspto-grants-1995_10
Patent number
US05462952

Reaction notes

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