Ethanol → [3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanone

HRID 1788069Notes

Reaction equation

HRID 1788069 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:7]=[C:8]([CH:12]2[C:21]3[CH:20]=[C:19]([C:22]([C:30]4[CH:35]=[CH:34][C:33](Cl)=[CH:32][CH:31]=4)(C4N(C)C=NC=4)[OH:23])[CH:18]=[CH:17][C:16]=3[NH:15]C3=NN=NN23)[CH:9]=[CH:10][CH:11]=1.[OH2:40].C[CH2:42][OH:43]>C(Cl)Cl>[Cl:5][C:6]1[CH:7]=[C:8]([C:12]2[O:40][N:15]=[C:16]3[CH:17]=[CH:18][C:19]([C:22]([C:30]4[CH:35]=[CH:34][C:33]([O:43][CH3:42])=[CH:32][CH:31]=4)=[O:23])=[CH:20][C:21]=23)[CH:9]=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 24386Thionyl ChlorideHCID 1360964279-(3-chlorophenyl)-alpha-(4-chlorophenyl)-4,9-dihydro-alpha-(1-methyl-1H-imidazol-5-yl)-tetrazolo[5,1-b]quinazoline-7-methanol

Product 1

HCID 17976096[3-(3-Chlorophenyl)-2,1-benzisoxazol-5-yl](4-methoxyphenyl)-methanoneYield 17%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Thionyl chloride (0.1 ml) was added at room temperature to a mixture of compound 1 (0.0002 mol) in EtOH (2 ml). The mixture was stirred at room temperature for 2 hours. Water was added. The mixture was taken up in DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.15 g) was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH 98/2). The pure fractions were collected and the solvent was evaporated. The residue (0.03 g) was taken up in DCM and evaporated till dryness, yielding 0.023 g (17%) of compound 10.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried (MgSO4)
  3. filtrationfiltered
  4. customthe solvent was evaporated
  5. customThe residue (0.15 g) was purified by column chromatography over kromasil® (10 μm) (eluent: DCM/MeOH 98/2)
  6. customThe pure fractions were collected
  7. customthe solvent was evaporated
  8. customevaporated till dryness

Sources & evidence

ORD record
ord-f0885ae53cdd40c0bc3e07fc5ec6fe31
Source dataset
uspto-grants-2009_03
Patent number
US07511138B2

Reaction notes

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