Triethylamine → (E)-4-[2-{2-[N-phenoxycarbonyl-N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine

HRID 858181Notes

Reaction equation

HRID 858181 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([S:9]([NH:12][C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=2/[CH:19]=[CH:20]/[C:21]2[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=2)(=[O:11])=[O:10])=[CH:5][CH:4]=1.[C:27](Cl)(=[O:35])[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(N(CC)CC)C>C(Cl)(Cl)Cl>[O:28]([C:27]([N:12]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=1/[CH:19]=[CH:20]/[C:21]1[CH:26]=[CH:25][N:24]=[CH:23][CH:22]=1)[S:9]([C:6]1[CH:5]=[CH:4][C:3]([O:2][CH3:1])=[CH:8][CH:7]=1)(=[O:11])=[O:10])=[O:35])[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 15891Phenyl chloroformateHCID 6366736Hmn 154

Product 1

HCID 12112542(E)-4-[2-{2-[N-phenoxycarbonyl-N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

1.00 g of (E)-4-[2-{2-[N-(4-methoxybenzenesulfonyl)amino]phenyl}ethenyl]pyridine was suspended in 40 ml of chloroform and, after adding 1.82 g of phenyl chlorocarbonate, 1.20 g of triethylamine was slowly added under ice cooling. Then, the mixture was stirred at room temperature for 5 minutes. The solvent was distilled off under reduced pressure and the desired product was purified by silica gel column (carrier: Wako Gel C200, developing solvent chloroform) to obtain the desired compound. The desired compound was treated with ethanol to obtain 0.71 g of a white granular crystal.

Workup

  1. additionwas slowly added under ice cooling
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe desired product was purified by silica gel column (carrier: Wako Gel C200, developing solvent chloroform)

Sources & evidence

ORD record
ord-6ce5e01135e941c89da989ea060eea91
Source dataset
uspto-grants-2006_12
Patent number
US07148244B2

Reaction notes

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