Dicyclohexylcarbodiimide → HCID 66616066, compound

HRID 2172158Notes

Reaction equation

HRID 2172158 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([OH:8])=O)#[N:2].ON1C2C=CC=CC=2N=N1.C1(N=C=NC2CCCCC2)CCCCC1.[NH:37]([C:39]1[CH:48]=[CH:47][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:41][CH:40]=1)[NH2:38]>ClCCl>[C:1]([C:3]1[CH:4]=[C:5]([CH:9]=[CH:10][CH:11]=1)[C:6]([NH:38][NH:37][C:39]1[CH:40]=[CH:41][C:42]([C:43]([O:45][CH3:46])=[O:44])=[CH:47][CH:48]=1)=[O:8])#[N:2]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 158753-Cyanobenzoic acidHCID 757711-HydroxybenzotriazoleHCID 408928Methyl 4-hydrazinylbenzoate

Product 1

HCID 66616066HCID 66616066, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

At 0° C., to a suspension of 3-cyanobenzoic acid (0.62 g, 4.2 mmol) in dichloromethane (15 mL) is added THE dropwise until the system became homogenous, which is followed by the addition of 1-hydroxybenzotriazole (0.57 g, 4.2 mmol) and dicyclohexylcarbodiimide (0.87 g, 4.2 mmol). The mixture is brought to room temperature slowly and stirred for 0.5 h. To the mixture, methyl 4-hydrazinobenzoate (0.63 g, 3.8 mmol) is added and the mixture is stirred for 2 hr. The precipitate is then removed by filtration and washed with dichloromethane. The filtrate is washed with water and brine, dried over anhydrous Na2SO4, which is discarded later. The crude product obtained after the removal of the solvent is separated by column chromatography (silica gel, 1:19 ethyl acetate-dichloromethane) to provide the intermediate, methyl 4-[2-(3-cyanobenzoyl)hydrazino]benzoate (0.68 g, 61%). MS (ES+) m/z: 296.

Workup

  1. additionis added THE dropwise until the system
  2. customis brought to room temperature
  3. stirringthe mixture is stirred for 2 hr
  4. customThe precipitate is then removed by filtration
  5. washwashed with dichloromethane
  6. washThe filtrate is washed with water and brine
  7. dry with materialdried over anhydrous Na2SO4, which
  8. customThe crude product obtained
  9. customafter the removal of the solvent
  10. customis separated by column chromatography (silica gel, 1:19 ethyl acetate-dichloromethane)

Sources & evidence

ORD record
ord-98bd46a7183040dc9e02dd37de652685
Source dataset
uspto-grants-2015_06
Patent number
US09051342B2

Reaction notes

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