Aniline → HCID 178462849, compound

HRID 40756Notes

Reaction equation

HRID 40756 reaction equation
[C:1]1(=[O:17])[N:5]([CH2:6][CH2:7][S:8](Cl)(=[O:10])=[O:9])[C:4](=[O:12])[C:3]2=[CH:13][CH:14]=[CH:15][CH:16]=[C:2]12.[NH2:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1>C(Cl)(Cl)Cl>[C:4]1(=[O:12])[N:5]([CH2:6][CH3:7])[C:1](=[O:17])[C:2]2=[CH:16][CH:15]=[CH:14][CH:13]=[C:3]12.[C:19]1([NH:18][SH:8](=[O:10])=[O:9])[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1

Participants

4

Reactant 2

HCID 6115AnilineHCID 3087392-Phthalimidoethanesulfonyl chloride

Product 1

HCID 178462849HCID 178462849, compoundYield 72.5%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-Phthalimidoethanesulfonyl chloride (2.0 g) was added in portions to a solution of aniline (2.3 g) in chloroform (15 ml) and the resulting mixture was stirred at room temperature for 16 hours. The organic phase was then washed with water and 1 M HCl. Removal of the solvent gave the crude product as a solid that was recrystallised from EtOH to yield 1.76 g (65%) of the title compound as a solid. 1H-NMR (CDCl3) δ (ppm) 7.87-7.83 (m, 2H), 7.77-7.70 (m, 2H), 7.32-7.10 (m, 5H), 4.09-4.03 (m, 2H), 3.47-3.41 (m, 2H).

Workup

  1. washThe organic phase was then washed with water and 1 M HCl
  2. customRemoval of the solvent
  3. customgave the crude product as a solid
  4. customthat was recrystallised from EtOH

Sources & evidence

ORD record
ord-c10b138d3a07497f92902ed4eb0920a8
Source dataset
uspto-grants-2013_09
Patent number
US08530486B2

Reaction notes

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