Potassium Carbonate → HCID 68539043, compound

HRID 1441511Notes

Reaction equation

HRID 1441511 reaction equation
[CH2:1]([O:3][C@:4]12[C@@H:17]3[N:18]([CH3:21])[CH2:19][CH2:20][C@:9]1([C:10]1[C:11]([OH:24])=[C:12]([O:22][CH3:23])[CH:13]=[CH:14][C:15]=1[CH2:16]3)[C@H:8]([CH3:25])[C:7](=[O:26])[CH2:6][CH2:5]2)[CH3:2].[C:27]([O-:30])([O-])=[O:28].[K+].[K+]>[Cl-].C1([N+](C)(C)C)C=CC=CC=1.O>[C:27]([OH:30])(=[O:28])[C:5]1[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=1)[OH:3].[CH2:1]([O:3][C@:4]12[C@@H:17]3[N:18]([CH3:21])[CH2:19][CH2:20][C@:9]1([C:10]1[C:11]([O:24][CH3:27])=[C:12]([O:22][CH3:23])[CH:13]=[CH:14][C:15]=1[CH2:16]3)[C@H:8]([CH3:25])[C:7](=[O:26])[CH2:6][CH2:5]2)[CH3:2]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 86619015HCID 86619015, compound

Product 1

HCID 68539043HCID 68539043, compound

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of the compound 33 (1.895 g, 5.3 mmol) (evaporation residue of the mother liquor, see above), K2CO3 (2.12 g, 15.3 mmol), phenyltrimethyl ammonium chloride (1.8 g, 10.5 mmol) and water free N,N-dimethylformamide (20 ml) was stirred at 80° C. (bath temperature) under N2 for 3 h. After filtration from the inorganic material and washing with dichloromethane, the filtrate was evaporated down. The evaporation residue was dissolved in dichloromethane, washed with water (2×50 ml) and saturated NaCl solution (1×50 ml), dried over sodium sulphate and evaporated down. The evaporation residue (2.11 g of dark brown oil) was purified using column chromatography (basic aluminium oxide, activity level III; dichloromethane). The evaporation residue was crystallised as compound 34.C7H6O3 with salicylic acid in diisopropylether. Yield: 1.32 g (49%). Fp. 135-141° C.; IR (KBr): 3400 (+NH, OH), 1710 (C═O), 1630 (CO2) cm−1; 1H-NMR (CDCl3): δ 7.88 (m, +NH), 7.27 (m, 2 arom. H), 6.81 (m, 4,arom. H), 3.86 (s, OCH3), 3.83 (s, OCH3), 2.84 (s, +NCH3), 1.40 (d, C5—CH3, 5.8 Hz), 1.17 (t, CH3CH2, J=5.3 Hz); MS (CI): m/z 374 (M++1).

Workup

  1. customevaporation residue of the mother liquor
  2. filtrationAfter filtration from the inorganic material
  3. washwashing with dichloromethane
  4. customthe filtrate was evaporated down
  5. dissolutionThe evaporation residue was dissolved in dichloromethane
  6. washwashed with water (2×50 ml) and saturated NaCl solution (1×50 ml)
  7. dry with materialdried over sodium sulphate
  8. customevaporated down
  9. customThe evaporation residue (2.11 g of dark brown oil) was purified
  10. customThe evaporation residue was crystallised as compound 34
  11. custom135-141° C.

Sources & evidence

ORD record
ord-5ed1e0ae94b54bb1aba973003f695477
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

Loading…