Hydrochloric Acid → HCID 67856162, compound

HRID 1588270Notes

Reaction equation

HRID 1588270 reaction equation
[H-].[Na+].[CH2:3]([O:5][C:6]([C:8]1[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:18])(=[O:17])[N:9]=1)=[O:7])[CH3:4].[Br:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[C:22]([F:28])[CH:21]=1.Cl.[CH2:30]([OH:32])[CH3:31]>CN(C=O)C.O>[CH2:3]([O:5][C:6]([C:8]1([O:32][CH2:30][CH3:31])[C:12]2[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=2[S:10](=[O:17])(=[O:18])[N:9]1[CH2:24][C:23]1[CH:26]=[CH:27][C:20]([Br:19])=[CH:21][C:22]=1[F:28])=[O:7])[CH3:4]

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 27336604-Bromo-2-fluorobenzyl bromideHCID 67856152HCID 67856152, compound

Product 1

HCID 67856162HCID 67856162, compoundYield 68%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (0.21 g, 7.02 mmol, 80% dispersion in mineral oil) was added to a stirred, room temperature solution of (VII) (1.40 g, 5.85 mmol) and dry ethanol (0.38 mL), 6.44 mmol) in DMF (8 mL). An exotherm resulted and after 10 min, 4-bromo-2-fluorobenzyl bromide (1.72 g, 6.44 mmol) was added. After 2 h, the reaction mixture was added to an aqueous solution consisting of 10% aq. HCl (25 mL) and water (125 mL). This was extracted with ether (150 mL) and the ether extract was washed with brine (150 mL) and silica gel (25 mL) was added to it. The ether was removed and the silica adsorbate was flash chromatographed (7:3 petroleum ether: ethyl acetate) to provide the title compound as an oil (1.89 g, 68%): NMR (CDCl3, 300 MHz): d 7.89 (m, 1H, ArH), 7.70 (m, 2H, ArH), 7.55 (m, 2H, ArH), 7.26 (m, 2H, ArH), 4.60 (d, 1H, J=16.7 Hz, NCH2), 4.50 (d, 1H, J=16.7 Hz, NCH2), 4.05 (m, 2H, CO2CH2), 3.22 (m, 1H, OCH2), 2.94 (m, 1H, OCH2), 1.11 (t, 3H, CH3), 1.05 (t, 3H, CH3); IR (neat, cm-1): 1750: MS (+FAB): 472, 474 (MH+, 5%), 426, 428 (35%), 398, 400 (20%), 187, 189 (100%).

Workup

  1. customAn exotherm resulted and after 10 min
  2. additionthe reaction mixture was added to an aqueous solution
  3. extractionThis was extracted with ether (150 mL)
  4. extractionthe ether extract
  5. washwas washed with brine (150 mL) and silica gel (25 mL)
  6. additionwas added to it
  7. customThe ether was removed
  8. customchromatographed (7:3 petroleum ether: ethyl acetate)

Sources & evidence

ORD record
ord-e41b1085cec74b42bc6c0961c097c328
Source dataset
uspto-grants-1993_06
Patent number
US05221686

Reaction notes

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