Thionyl Chloride → HCID 20478449, compound

HRID 904683Notes

Reaction equation

HRID 904683 reaction equation
O[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:10]3=2)[N:5]=[C:4]([C:22]([O:24][CH3:25])=[O:23])[CH:3]=1.S(Cl)([Cl:28])=O>ClC(Cl)C.CN(C)C=O>[Cl:28][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]3[O:15][C:14]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[CH:13][C:12](=[O:21])[C:10]3=2)[N:5]=[C:4]([C:22]([O:24][CH3:25])=[O:23])[CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl Chloride2×HCID 178469284HCID 178469284, compound

Product 1

HCID 20478449HCID 20478449, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 63651,1-DichloroethaneSolvent

Procedure

The product of step (a) (1.35 g; 3.9 mmole) suspended in dichloroethane was treated with thionyl chloride (0.9 g; 7.5 mmole) and dimethylformamide (4 drops). The mixture was heated under reflux for 6 hrs adding more thionyl chloride (0.2 ml) after 3 hrs. The mixture was evaporated to dryness and triturated with ether to give a buff solid (1.35 g; 96%), mp 193° shown to be the title compound by its NMR and mass spectrum.

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 6 hrs
  3. customThe mixture was evaporated to dryness
  4. customtriturated with ether
  5. customto give a buff solid (1.35 g; 96%), mp 193°

Sources & evidence

ORD record
ord-80803fd4db0041ffb10506972b702b67
Source dataset
uspto-grants-1983_12
Patent number
US04419352

Reaction notes

Loading…