Diethyl Ether → HCID 18919381, compound

HRID 1290829Notes

Reaction equation

HRID 1290829 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]([N:12]([C:30](=[O:33])[CH2:31][CH3:32])[C:13]1[C:18]([S:19](O)(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)[CH2:10][CH3:11].P(Cl)(Cl)(Cl)(Cl)[Cl:35].CCOCC>ClCCl>[O:8]=[C:9]([N:12]([C:30](=[O:33])[CH2:31][CH3:32])[C:13]1[C:18]([S:19]([Cl:35])(=[O:21])=[O:20])=[CH:17][CH:16]=[CH:15][C:14]=1[C:23]1[CH:28]=[CH:27][CH:26]=[C:25]([CH3:29])[CH:24]=1)[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 18919384HCID 18919384, compound

Product 1

HCID 18919381HCID 18919381, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 3.6 g (7.6 mmol) of the N,N-diethylethanamine salt of 2-[bis(1-oxopropyl)amino]-3'-methyl[1,1'-biphenyl]-3-sulphonic acid in 8 ml of dichloromethane, at 0° C., are added 1.6 g (7.6 mmol) of phosphorus pentachloride and the mixture is allowed to return to room temperature. The mixture is then heated for 4 hours at the reflux temperature and is then allowed to return to room temperature. Ether is added, the mixture is filtered, the filtrate is concentrated and the residue is purified on a column of florisil™, eluting with an ether/pentane mixture (1/1). The product is recrystallized from an ether/pentane mixture.

Workup

  1. customto return to room temperature
  2. temperatureThe mixture is then heated for 4 hours at the reflux temperature
  3. customto return to room temperature
  4. filtrationthe mixture is filtered
  5. concentrationthe filtrate is concentrated
  6. customthe residue is purified on a column of florisil™
  7. washeluting with an ether/pentane mixture (1/1)
  8. customThe product is recrystallized from an ether/pentane mixture

Sources & evidence

ORD record
ord-18aea934e90e456485d7f805620e47fc
Source dataset
uspto-grants-1998_05
Patent number
US05753667

Reaction notes

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