Hydrochloric Acid → HCID 54395392, compound

HRID 2268854Notes

Reaction equation

HRID 2268854 reaction equation
[Br-].[CH3:2][O:3][C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[CH:9]([P+](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[O:8][C:7]2=[O:32].[Cl:33][C:34]1[CH:35]=[N:36][CH:37]=[C:38]([Cl:42])[C:39]=1[CH:40]=O.C(N(CC)CC)C.Cl>C(Cl)Cl>[Cl:33][C:34]1[CH:35]=[N:36][CH:37]=[C:38]([Cl:42])[C:39]=1[CH:40]=[C:9]1[C:10]2[C:6](=[CH:5][C:4]([O:3][CH3:2])=[CH:12][CH:11]=2)[C:7](=[O:32])[O:8]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 27629883,5-Dichloro-4-pyridinecarboxaldehydeHCID 11562468(5-Methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)triphenyl phosphonium bromide

Product 1

HCID 54395392HCID 54395392, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension under N2 of (5-methoxy-3-oxo-1,3-dihydro-isobenzofuran-1-yl)-triphenyl-phosphonium bromide (74 g, 0.134 mole), prepared as described in example 36, and 3,5-dichloro-pyridin-4-carbaldehyde (23.6 g, 0.134 mole) in CH2Cl2 (500 ml) was dropwise added with triethylamine (18.5 ml, 0.134 mole), adjusting the temperature with a water bath. The mixture was stirred overnight, then cooled and treated with 5% HCl. The phases were separated and the acidic one was extracted with CH2Cl2, washed with H2O/NaCl, discoloured with charcoal, anhydrified and concentrated at high vacuum. There were obtained 85.4 g of a crude which was used as such in the subsequent step. A sample of the crude was purified by flash chromatography (eluent: hexane/ethyl acetate 1:1).

Workup

  1. temperaturecooled
  2. customThe phases were separated
  3. extractionthe acidic one was extracted with CH2Cl2
  4. washwashed with H2O/NaCl
  5. concentrationconcentrated at high vacuum
  6. customThere were obtained 85.4 g of a crude which
  7. customA sample of the crude was purified by flash chromatography (eluent: hexane/ethyl acetate 1:1)

Sources & evidence

ORD record
ord-f563791359134c76888698789f480373
Source dataset
uspto-grants-2001_12
Patent number
US06329370B1

Reaction notes

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