Diethyl Ether → HCID 23448145, compound

HRID 1290830Notes

Reaction equation

HRID 1290830 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]([N:12]([C:25](=[O:28])[CH2:26][CH3:27])[C:13]1[C:18]([I:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=1[S:21](O)(=[O:23])=[O:22])[CH2:10][CH3:11].P(Cl)(Cl)(Cl)(Cl)[Cl:30].CCOCC>ClCCl>[O:8]=[C:9]([N:12]([C:25](=[O:28])[CH2:26][CH3:27])[C:13]1[C:18]([I:19])=[CH:17][C:16]([Br:20])=[CH:15][C:14]=1[S:21]([Cl:30])(=[O:23])=[O:22])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 18919380HCID 18919380, compound

Product 1

HCID 23448145HCID 23448145, compoundYield 43%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 32.5 g (55 mmol) of the N,N-diethylethanamine salt of 2-[bis(1-oxopropyl)amino]-5-bromo-3-iodobenzenesulphonic acid in dichloromethane are added portionwise, at 0° C. under nitrogen, 16.8 g (82.4 mmol) of phosphorus pentachloride. The mixture is allowed to warm to room temperature and is heated for 4 hours at the reflux temperature. 200 ml of ether are poured in, the mixture is filtered and the filtrate is concentrated. The residue is purified by chromatography on a column of florisil™ eluting with an ether/hexane mixture (2/8). The product is recrystallized from an ether/pentane mixture. 12 g of product are obtained in the form of white crystals.

Workup

  1. temperatureis heated for 4 hours at the reflux temperature
  2. filtrationis filtered
  3. concentrationthe filtrate is concentrated
  4. customThe residue is purified by chromatography on a column of florisil™
  5. washeluting with an ether/hexane mixture (2/8)
  6. customThe product is recrystallized from an ether/pentane mixture

Sources & evidence

ORD record
ord-50bf41c3778d4c8894edbeb9683e855a
Source dataset
uspto-grants-1998_05
Patent number
US05753667

Reaction notes

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