Sodium Bicarbonate → HCID 20583279, compound

HRID 411196Notes

Reaction equation

HRID 411196 reaction equation
[Cl:1][C:2]1[CH:21]=[CH:20][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][CH:16]=[CH:15][C:14]=3[C:18]=2[OH:19])=[O:9])=[CH:4][CH:3]=1.[Cl-].[CH2:23]=[N+:24]1[CH2:29][CH2:28][O:27][CH2:26][CH2:25]1.C(=O)(O)[O-].[Na+]>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:6][NH:7][C:8]([C:10]2[CH:11]=[CH:12][C:13]3[S:17][C:16]([CH2:23][N:24]4[CH2:29][CH2:28][O:27][CH2:26][CH2:25]4)=[CH:15][C:14]=3[C:18]=2[OH:19])=[O:9])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11367014Morpholinium, 4-methylene-, chlorideHCID 69731216HCID 69731216, compound

Product 1

HCID 20583279HCID 20583279, compoundYield 76%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of N-(4-chlorobenzyl)-4-hydroxy-1-benzothiophene-5-carboxamide (Preparation 14, 0.15 g), 4-methylenemorpholin4-ium chloride (0.13 g), and anhydrous acetonitrile (5 mL) is heated at reflux for 2 hours. Upon cooling, a saturated solution of sodium bicarbonate is added until the pH=9 and this solution is partitioned between ethyl acetate (50 mL) and water (50 mL). The organic layer is washed with brine, dried over Na2SO4, filtered, and concentrated to give a pink oil. Chromatography on a Biotage column eluting with 20% ethyl acetate in heptane (250 mL) and 50% ethyl acetate in heptane (500 mL) affords 140 mg (76%) of the title compound as a white solid. Physical characteristics: Mp 200° C.; MS (ESI+) for C21H21ClN2O3S m/z 417 (M+H)+.

Workup

  1. temperatureis heated
  2. temperatureat reflux for 2 hours
  3. temperatureUpon cooling
  4. customthis solution is partitioned between ethyl acetate (50 mL) and water (50 mL)
  5. washThe organic layer is washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customto give a pink oil
  10. washChromatography on a Biotage column eluting with 20% ethyl acetate in heptane (250 mL) and 50% ethyl acetate in heptane (500 mL)

Sources & evidence

ORD record
ord-f244526dbe4c47e0ab2a0337c68480e1
Source dataset
uspto-grants-2003_05
Patent number
US06559145B2

Reaction notes

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