Potassium Bromide → HCID 53638373, compound

HRID 1707737Notes

Reaction equation

HRID 1707737 reaction equation
C([Li])CCC.[O:6]1[CH2:11][CH2:10][N:9]([CH2:12][CH2:13][O:14][C:15]2[CH:20]=[CH:19][C:18](Br)=[CH:17][CH:16]=2)[CH2:8][CH2:7]1.[Cl:22][C:23]1[CH:41]=[CH:40][C:26]([CH:27]=[C:28]2[C:32](=[O:33])[C:31]3[CH:34]=[CH:35][C:36]([O:38][CH3:39])=[CH:37][C:30]=3[O:29]2)=[CH:25][CH:24]=1.[K+].[Br-]>C1COCC1>[Cl:22][C:23]1[CH:24]=[CH:25][C:26]([CH:27]=[C:28]2[O:29][C:30]3[CH:37]=[C:36]([O:38][CH3:39])[CH:35]=[CH:34][C:31]=3[C:32]2([C:18]2[CH:19]=[CH:20][C:15]([O:14][CH2:13][CH2:12][N:9]3[CH2:10][CH2:11][O:6][CH2:7][CH2:8]3)=[CH:16][CH:17]=2)[OH:33])=[CH:40][CH:41]=1

Participants

6

Reactant 4

HCID 253877Potassium BromideHCID 9078073(2H)-Benzofuranone, 2-[(4-chlorophenyl)methylene]-6-methoxy-HCID 20538154-(2-(4-Bromophenoxy)ethyl)morpholineHCID 178418339Butyllithium

Product 1

HCID 53638373HCID 53638373, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

n-Butyl lithium (2.87 mi of a 1.28M solution, 3.68 mmol) was added dropwise to a solution of 4-[2-morpholinoethoxy]phenyl bromide (0.80 ml, 3.68 mmol) in THF (10 ml) at -78° C. under nitrogen atmosphere. After stirring for 1 hour at -78° C., 2-(p-chlorobenzylidene)-6-methoxy-3(2H)-benzofuranone (1.0 g, 3.50 mmol) in THF (5 m was added dropwise to the mixture at -78° C. The reaction mixture was left overnight at room temperature. It was quenched with saturated ammonium chloride, THF was evaporated off to yield an oil which was extracted with ethyl acetate (2×20 ml). The ethyl acetate extract was washed with water followed by brine (2×20 ml), dried (anhydrous magnesium sulfate) and the solvent was evaporated to give an oil which was chromatographed on silica gel. Elution with (chloroform:hexane:triethylamine=1:1:0.2) yielded a solid of the free base (Rf =0.3). Yield (56%); m.p. 69-70° C.; 1H-NMR (CDCl3) δ 1.55 (brs, 1H, OH), 2.54-2.58 (m, 4H, N(CH2CH2)20 (ring)), 2.79 (t, 2H, OCH2CH2N), 3.7-3.74 (m, 4H, N(CH2CH2)2 (ring)), 3.84 (3H, OCH3), 4.09 (2H, OCH2CH2N), 5.64 (benzylidene proton), 6.72-7.60 (m, 11H, ArH). 13C-NMR δ(ppm) 104.4 (benzylidene carbon), 133.1 (C-2), 81.0 (C-3), 54.1 (OCH3); IR (KBr) 1680 cm-1 (C=C), 3400 cm-1 (broad OH); m/z (%) 495(5), 493(10), 100(100). (Found: C, 68.14, H, 5.89, N, 2.75, Cl, 7.30. C28H28ClO5N required C, 68.15, It, 5.68, N, 2.84, Cl, 7.10).

Workup

  1. waitThe reaction mixture was left overnight at room temperature
  2. customIt was quenched with saturated ammonium chloride, THF
  3. customwas evaporated off
  4. customto yield an oil which
  5. extractionwas extracted with ethyl acetate (2×20 ml)
  6. extractionThe ethyl acetate extract
  7. washwas washed with water
  8. dry with materialdried (anhydrous magnesium sulfate)
  9. customthe solvent was evaporated
  10. customto give an oil which
  11. customwas chromatographed on silica gel
  12. washElution with (chloroform:hexane:triethylamine=1:1:0.2)
  13. customyielded a solid of the free base (Rf =0.3)
  14. customYield (56%)

Sources & evidence

ORD record
ord-52b9385826c54f9d9234b5ffa2aaa39e
Source dataset
uspto-grants-1994_10
Patent number
US05354861

Reaction notes

Loading…