Hydrochloric Acid → HCID 392893, compound

HRID 1250221Notes

Reaction equation

HRID 1250221 reaction equation
C[O:2][C:3]1[C:15]2[CH:14]=[CH:13][S:12][C:11]=2[C:10]([O:16]C)=[C:9]2[C:4]=1[CH:5]=[CH:6][CH:7]=[CH:8]2.[C:18](Cl)(=[O:20])[CH3:19].[Al+3].[Cl-].[Cl-].[Cl-].Cl>ClCCCl.CC(O)C.CC(O)=O>[C:18]([C:13]1[S:12][C:11]2[C:10](=[O:16])[C:9]3[C:4]([C:3](=[O:2])[C:15]=2[CH:14]=1)=[CH:5][CH:6]=[CH:7][CH:8]=3)(=[O:20])[CH3:19]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 6367Acetyl chlorideHCID 6451240Aluminum(III) ChlorideHCID 18327690HCID 18327690, compound

Product 1

HCID 392893HCID 392893, compound

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
5 °C

Procedure

To 4 (1.5 g) in 1,2-dichloroethane (120 mL) were added acetyl chloride (4.3 mL, 55 mmol) and AlCl3 (7.3 g, 55 mmol). The resulting mixture was stirred at 5±2° C. for 4 h and then poured into ice water and acidified with conc. HCl. The organic layer was washed with water, dried over anhydrous MgSO4 and evaporated. CrO3 (0.5 g, 50 mmol) and HOAc (12 mL) were added to the residue. The mixture was stirred at room temperature for 8 h, and then i-PrOH (30 mL) was added, and the resulting solution extracted with CHCl3. The organic layer was washed with saturated NaHCO3, dried over anhydrous MgSO4 and evaporated. Column chromatography (silica gel, CHCl3) gave compounds 5, 6, and 7 in 20, 11, and 9% yields, respectively.

Workup

  1. washThe organic layer was washed with water
  2. dry with materialdried over anhydrous MgSO4
  3. customevaporated
  4. stirringThe mixture was stirred at room temperature for 8 h
  5. extractionthe resulting solution extracted with CHCl3
  6. washThe organic layer was washed with saturated NaHCO3
  7. dry with materialdried over anhydrous MgSO4
  8. customevaporated

Sources & evidence

ORD record
ord-f9843b426eaf4d8aadd5454773f71c0b
Source dataset
uspto-grants-2002_01
Patent number
US06337346B1

Reaction notes

Loading…