Thionyl Chloride → HCID 22734088, compound

HRID 1057867Notes

Reaction equation

HRID 1057867 reaction equation
[C:1]([CH2:4][CH:5]1[C:9]2[C:10]([C:16]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=3[Cl:26])=[O:17])=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:8]=2[O:7][CH2:6]1)([OH:3])=[O:2].S(Cl)(Cl)=O>ClCCl>[CH2:5]([O:2][C:1]([CH2:4][CH:5]1[C:9]2[C:10]([C:16]([NH:18][C:19]3[C:24]([Cl:25])=[CH:23][N:22]=[CH:21][C:20]=3[Cl:26])=[O:17])=[CH:11][CH:12]=[C:13]([O:14][CH3:15])[C:8]=2[O:7][CH2:6]1)=[O:3])[C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][CH:8]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22734342(+/-)-3-Carboxymethyl-4-(3,5-dichloro-4-pyridylamino-carbonyl)-7-methoxy-2,3-dihydrobenzofuran

Product 1

HCID 22734088HCID 22734088, compoundYield 85.2%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound 9 (0.291 g) obtained in Example 9 was dissolved in dichloromethane (2.9 ml) and thionyl chloride (1.5 ml) was added thereto, followed by stirring at room temperature for one hour. The solvent was distilled off under reduced pressure, the residue was again dissolved in toluene, and the solvent was distilled off under reduced pressure. Benzyl alcohol (2 ml) was added to the residue followed by heating under reflux for 30 minutes. The reaction solution was concentrated and the residue was recrystallized from ethanol to give Compound 13 (0.3.04 g, 85.2%) as a white solid.

Workup

  1. distillationThe solvent was distilled off under reduced pressure
  2. dissolutionthe residue was again dissolved in toluene
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionBenzyl alcohol (2 ml) was added to the residue
  5. temperatureby heating
  6. temperatureunder reflux for 30 minutes
  7. concentrationThe reaction solution was concentrated
  8. customthe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-26d12f2a85674a718f66d8a16e60ba2b
Source dataset
uspto-grants-2003_02
Patent number
US06514996B2

Reaction notes

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