Diethyl Ether → HCID 23448078, compound

HRID 1450366Notes

Reaction equation

HRID 1450366 reaction equation
C(N(CC)CC)C.[O:8]=[C:9]([N:12]([C:28](=[O:31])[CH2:29][CH3:30])[C:13]1[C:18]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:17][CH:16]=[CH:15][C:14]=1[S:24](O)(=[O:26])=[O:25])[CH2:10][CH3:11].P(Cl)(Cl)(Cl)(Cl)[Cl:33].CCOCC>ClCCl>[O:8]=[C:9]([N:12]([C:28](=[O:31])[CH2:29][CH3:30])[C:13]1[C:18]([C:19]2[S:20][CH:21]=[CH:22][CH:23]=2)=[CH:17][CH:16]=[CH:15][C:14]=1[S:24]([Cl:33])(=[O:26])=[O:25])[CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 3283Diethyl EtherHCID 8471TriethylamineHCID 24819Phosphorus pentachlorideHCID 18919383HCID 18919383, compound

Product 1

HCID 23448078HCID 23448078, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2.8 g (6.1 mmol) of the N,N-diethylethanamine salt of 2-[bis(1-oxopropyl)amino]-3-thien-2-ylbenzenesulphonic acid in 6 ml of dichloromethane are added, at 0° C., 1.3 g (6.1 mmol) of phosphorus pentachloride and the reaction mixture is allowed to warm to room temperature. The mixture is then heated for 5 hours at the reflux temperature and then allowed to cool to room temperature. Ether is added, the mixture is filtered and the residue is precipitated from an ether/pentane mixture (1/1). The mixture is filtered and the filtrate is concentrated under reduced pressure and purified by chromatography on a column of florisil™. 2.2 g of product are obtained, which product is crystallized from an ether/pentane mixture.

Workup

  1. temperatureThe mixture is then heated for 5 hours at the reflux temperature
  2. temperatureto cool to room temperature
  3. filtrationthe mixture is filtered
  4. customthe residue is precipitated from an ether/pentane mixture (1/1)
  5. filtrationThe mixture is filtered
  6. concentrationthe filtrate is concentrated under reduced pressure
  7. custompurified by chromatography on a column of florisil™

Sources & evidence

ORD record
ord-3bf15fecf3a24cf58948848ffb271394
Source dataset
uspto-grants-1997_02
Patent number
US05602149

Reaction notes

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