Diisopropylethylamine → 4-(3-(3-cyanophenyl)ureido)-N-(2,3,6-trifluorobenzyl)benzenesulfonamide

HRID 497315Notes

Reaction equation

HRID 497315 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:22])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18](Cl)(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2].[F:23][C:24]1[C:31]([F:32])=[CH:30][CH:29]=[C:28]([F:33])[C:25]=1[CH2:26][NH2:27].CCN(C(C)C)C(C)C>C1COCC1>[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10](=[O:22])[NH:11][C:12]2[CH:17]=[CH:16][C:15]([S:18]([NH:27][CH2:26][C:25]3[C:28]([F:33])=[CH:29][CH:30]=[C:31]([F:32])[C:24]=3[F:23])(=[O:20])=[O:19])=[CH:14][CH:13]=2)[CH:6]=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27770432,3,6-TrifluorobenzylamineHCID 22318884HCID 22318884, compound

Product 1

HCID 223189094-(3-(3-cyanophenyl)ureido)-N-(2,3,6-trifluorobenzyl)benzenesulfonamideYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

4-[3-(3-Cyanophenyl)-ureido]-benzenesulfonyl chloride (1.0 g, 2.98 mmol) was dissolved in 20 ml THF, 2,3,6-trifluoro-benzylamine (0.48 g, 2.98 mmol) and DIEA (0.52 ml, 2.98 mmol) were added and the solution was refluxed for about 3 h. The solvent was removed in vacuo and the residue cristallized with ethanol/water. The solid was filtered and dried in vacuo. Yield 94% of 4-[3-(3-cyano-phenyl)-ureido]-N-(2,3,6-trifluorobenzyl)-benzenesulfonamide.

Workup

  1. temperaturethe solution was refluxed for about 3 h
  2. customThe solvent was removed in vacuo
  3. filtrationThe solid was filtered
  4. customdried in vacuo

Sources & evidence

ORD record
ord-47c449033ea24b609a205cc8747c97d0
Source dataset
uspto-grants-2005_09
Patent number
US06949567B2

Reaction notes

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