Pyridine → HCID 23103069, compound

HRID 1625596Notes

Reaction equation

HRID 1625596 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([Cl:8])=[O:7].[N:16]1[CH:21]=CC=[CH:18][CH:17]=1.C(OCC)(=[O:24])C>>[ClH:8].[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:9]=[C:10]([O:14][CH3:15])[C:11]=1[O:12][CH3:13])[C:6]([O:24][CH2:18][CH2:17][NH:16][CH3:21])=[O:7]

Participants

4

Reactant 3

HCID 1049Pyridine2×HCID 8857Ethyl Acetate2×HCID 78282Benzoyl chloride, 3,4,5-trimethoxy-2×

Product 1

HCID 23103069HCID 23103069, compound

Conditions

Temperature
60 °C

Procedure

To a mixture of tert-butyl 2-hydroxyethyl (methyl)carbamate (1.75 g) obtained in Reference Example 1 and ethyl acetate (10 mL) were added 3,4,5-trimethoxybenzoyl chloride (2.54 g) and pyridine (0.97 mL). After stirring at 60° C. for 14 hrs., 3,4,5-trimethoxybenzoyl chloride (1.30 g), pyridine (0.97 mL) and ethyl acetate (10 mL) were added, and the mixture was stirred at 60° C. for 24 hrs. The reaction mixture was filtered and ethyl acetate (50 mL) and water (30 mL) were added to the filtrate. After partitioning, ethyl acetate layer was washed with 1N hydrochloric acid (30 mL), water (30 mL), an aqueous copper (II) sulfate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate.

Workup

  1. stirringthe mixture was stirred at 60° C. for 24 hrs
  2. filtrationThe reaction mixture was filtered
  3. additionethyl acetate (50 mL) and water (30 mL) were added to the filtrate
  4. customAfter partitioning
  5. washethyl acetate layer was washed with 1N hydrochloric acid (30 mL), water (30 mL)
  6. dry with materialan aqueous copper (II) sulfate solution (30 mL), water (30 mL) and saturated brine (30 mL), and dried over anhydrous magnesium sulfate

Sources & evidence

ORD record
ord-5c918db0d1c246519a117d4c4928096d
Source dataset
uspto-grants-2014_07
Patent number
US08784885B2

Reaction notes

Loading…