Triethylamine → ethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarboximidate

HRID 2198429Notes

Reaction equation

HRID 2198429 reaction equation
[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[NH:8])[O:5][CH2:6][CH3:7].[Cl:13][C:14]1[CH:15]=[C:16]([N:31]=[C:32]=[O:33])[CH:17]=[C:18]([Cl:30])[C:19]=1[O:20][C:21]1[CH:26]=[CH:25][C:24]([N+:27]([O-:29])=[O:28])=[CH:23][CH:22]=1.C(N(CC)CC)C>CC(C)=O>[Cl:1][C:2]1[CH:12]=[CH:11][CH:10]=[CH:9][C:3]=1[C:4](=[N:8][C:32]([NH:31][C:16]1[CH:17]=[C:18]([Cl:30])[C:19]([O:20][C:21]2[CH:22]=[CH:23][C:24]([N+:27]([O-:29])=[O:28])=[CH:25][CH:26]=2)=[C:14]([Cl:13])[CH:15]=1)=[O:33])[O:5][CH2:6][CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 13092607Ethyl 2-chlorobenzimidateHCID 130926093,5-Dichloro-4-(4-nitrophenoxy)phenylisocyanate

Product 1

HCID 53641175ethyl 2-chloro-N-[[[3,5-dichloro-4-(4-nitrophenoxy)phenyl]amino]carbonyl]benzenecarboximidate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of ethyl 2-chlorobenzimidate hydrofluoroborate (1.90 g., 7.00 mmol), 3,5-dichloro-4-(4-nitrophenoxy)phenylisocyanate (2.28 g., 7.00 mmol) and triethylamine (0.72 g., 7.20 mmol) in acetone (20 ml) is stirred at room temperature for four hours under an atmosphere of dry nitrogen. The reaction mixture is concentrated under reduced pressure and the residue partitioned between ethyl acetate and water. The organic phase is washed sequentially with dilute hydrochloric acid, dilute sodium bicarbonate, and brine. After drying over sodium sulfate, the ethyl acetate solution is concentrated under reduced pressure and the residue chromatographed over silica gel eluting with 20% ethyl acetate in hexane. The product fractions are combined and concentrated under reduced pressure to leave the title compound as an amorphous solid.

Workup

  1. concentrationThe reaction mixture is concentrated under reduced pressure
  2. customthe residue partitioned between ethyl acetate and water
  3. washThe organic phase is washed sequentially with dilute hydrochloric acid, dilute sodium bicarbonate, and brine
  4. dry with materialAfter drying over sodium sulfate
  5. concentrationthe ethyl acetate solution is concentrated under reduced pressure
  6. customthe residue chromatographed over silica gel eluting with 20% ethyl acetate in hexane
  7. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-4600534be54849d1900df576fc0a4526
Source dataset
uspto-grants-1982_11
Patent number
US04357347

Reaction notes

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