Potassium Carbonate → HCID 68539007, compound

HRID 1441510Notes

Reaction equation

HRID 1441510 reaction equation
[OH:1][C:2]1[C:15]2[C@:14]34[CH2:16][CH2:17][N:18]([CH3:19])[C@@H:8]([C@:9]3([O:21][CH2:22][CH2:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4)[CH2:7][C:6]=2[CH:5]=[CH:4][C:3]=1[O:31][CH3:32].[C:33]([O-:36])([O-])=[O:34].[K+].[K+].[K+].[Br-]>[Cl-].C1([N+](C)(C)C)C=CC=CC=1.O>[C:33]([OH:36])(=[O:34])[C:3]1[C:2](=[CH:15][CH:6]=[CH:5][CH:4]=1)[OH:1].[CH3:32][O:31][C:3]1[CH:4]=[CH:5][C:6]2[CH2:7][C@H:8]3[N:18]([CH3:19])[CH2:17][CH2:16][C@@:14]4([C:15]=2[C:2]=1[O:1][CH3:33])[C@@:9]3([O:21][CH2:22][CH2:23][CH2:24][C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1)[CH2:10][CH2:11][C:12](=[O:20])[CH2:13]4

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 253877Potassium BromideHCID 86600279HCID 86600279, compound

Product 1

HCID 68539007HCID 68539007, compound

Reagents, catalysts & solvents 2

HCID 67309Phenyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of compound 25 (200 mg, 0.5 mmol), K2CO3 (420 mg, 3.0 mmol) and phenyltrimethyl ammonium chloride (254 mg, 1.5 mmol) and 50 ml water-free N,N-dimethylformamide was stirred for 9 h at 80° C. (bath temperature) under N2. After filtration from the inorganic residue, the filtrate was evaporated down, and the evaporation residue was purified using column chromatography (silica gel; CH2Cl2/MeOH/conc. NH4OH (93:7:1)). The evaporation residue (250 mg of foamy resin) was dissolved in MeOH and salicylic acid added to it. 102 mg (41%) of the compound 26.C7H6O3 was isolated. Fp. 110-115° C.; IR (KBr): 1720 (CO) cm−1; 1H-NMR (CDCl3): δ 7.29-7.18 (m, 5 arom. H), 6.75, (s, 2 arom. H), 3.93 (s, C4—OCH3), 3.80 (s, C3—OCH3), 2.31 (s, NCH3); MS (CI): m/z 450 (M++1).

Workup

  1. filtrationAfter filtration from the inorganic residue
  2. customthe filtrate was evaporated down
  3. customthe evaporation residue was purified
  4. dissolutionThe evaporation residue (250 mg of foamy resin) was dissolved in MeOH
  5. additionsalicylic acid added to it
  6. customC7H6O3 was isolated
  7. custom110-115° C.

Sources & evidence

ORD record
ord-14053594dbe1433b83849d4fc30ec326
Source dataset
uspto-grants-2010_02
Patent number
US07655671B2

Reaction notes

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