Sodium Iodide → HCID 22049694, compound

HRID 1830868Notes

Reaction equation

HRID 1830868 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[N:15]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3Cl)[S:17][CH:18]=2)=[CH:10][CH:9]=1.[I-].[Na+]>>[Cl:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[N:15]=[C:16]([C:19]3[CH:20]=[N:21][CH:22]=[CH:23][C:24]=3[N:1]3[CH2:6][CH2:5][O:4][CH2:3][CH2:2]3)[S:17][CH:18]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 3

HCID 5238Sodium IodideHCID 8083MorpholineHCID 220496904-Chloro-3-[4-(4-chlorophenyl)-2-thiazolyl]pyridine

Product 1

HCID 22049694HCID 22049694, compoundYield 67%

Conditions

Temperature
80 °C

Procedure

Morpholine (5 ml) was added to compound (43) (120 mg, 0.40 mmol) and sodium iodide (156 mg, 0.40 mmol). The reaction mixture was heated to 80° C. and stirred for 6 hrs. The solvent was evaporated under reduced pressure, and the obtained residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate. The aqueous layer was extracted with ethyl acetate. The extracts were combined, dried (MgSO4) and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography, and crystallized from ethyl acetate-n-hexane to give white crystals (100 mg, 67%).

Workup

  1. customThe solvent was evaporated under reduced pressure
  2. customthe obtained residue was partitioned between ethyl acetate and aqueous sodium hydrogen carbonate
  3. extractionThe aqueous layer was extracted with ethyl acetate
  4. dry with materialdried (MgSO4)
  5. customthe solvent was evaporated under reduced pressure
  6. customThe residue was purified by silica gel column chromatography
  7. customcrystallized from ethyl acetate-n-hexane

Sources & evidence

ORD record
ord-993a96745ec84bf88221c55aa0dad196
Source dataset
uspto-grants-2006_06
Patent number
US07067537B2

Reaction notes

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