Potassium → HCID 10278294, compound

HRID 860801Notes

Reaction equation

HRID 860801 reaction equation
[K].Br[CH2:3][C:4]([NH:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]([C:21]2[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=2)([OH:20])[C:14]2[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=2)=[CH:9][C:8]=1[CH:28]([C:30]1[CH:35]=[CH:34][CH:33]=[C:32]([Cl:36])[CH:31]=1)[OH:29])=[O:5]>CC(O)C>[Cl:36][C:32]1[CH:31]=[C:30]([CH:28]2[C:8]3[CH:9]=[C:10]([C:13]([C:21]4[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=4)([OH:20])[C:14]4[N:18]([CH3:19])[CH:17]=[N:16][CH:15]=4)[CH:11]=[CH:12][C:7]=3[NH:6][C:4](=[O:5])[CH2:3][O:29]2)[CH:35]=[CH:34][CH:33]=1

Participants

4

Reactant 2

HCID 5462222PotassiumHCID 69019215HCID 69019215, compound

Product 1

HCID 10278294HCID 10278294, compoundYield 11%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

2-methyl, 2-propanol, potassium salt (0.044 mol) was added to a mixture of intermediate (2) (0.011 mol) in 2-propanol (160 ml). The mixture was stirred for 48 hours, hydrolized and extracted with DCM and methanol. The organic layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (4.1 g) was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 90/10/1 and 85/15/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone and diethyl ether. The precipitate was filtered off and dried, yielding 0.58 g (11%) of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)hydroxy(1-methyl-1H-imidazol-5-yl)methyl]-1,5-dihydro-4,1-benzoxazepin-2(3H)-one, mp. 260° C.

Workup

  1. extractionhydrolized and extracted with DCM and methanol
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (4.1 g) was purified by column chromatography over silica gel (eluent: toluene/2-propanol/NH4OH 90/10/1 and 85/15/1; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from 2-propanone and diethyl ether
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-9733b6fe4044484ba09141af6860c22e
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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