Thionyl Chloride → HCID 22734088, compound

HRID 2084751Notes

Reaction equation

HRID 2084751 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 170.3%

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 (0.304 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-dbf8fcdbd00344d9bc38d5929711a115
Source dataset
uspto-grants-2004_04
Patent number
US06716987B1

Reaction notes

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