Potassium Carbonate → HCID 69023459, compound

HRID 860811Notes

Reaction equation

HRID 860811 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:14]3[CH:15]=[C:16]([C:19]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)([C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[OH:20])[CH:17]=[CH:18][C:13]=3[N:12]=[C:11]([NH:34][NH2:35])[CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1.[N:36]([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>Cl.O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:14]3[CH:15]=[C:16]([C:19]([C:27]4[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=4)([C:21]4[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=4)[OH:20])[CH:17]=[CH:18][C:13]=3[N:12]3[N:36]=[N:35][N:34]=[C:11]3[CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 69019256HCID 69019256, compound

Product 1

HCID 69023459HCID 69023459, compoundYield 23.2%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 5-(3-chlorophenyl)-α-(4-chlorophenyl)-2-hydrazino-3,5-dihydro-α-(1-methyl-1H-imidazol-5-yl)-4,1-benzothiazepine-7-methanol (described in Example B15a) (0.0082 mol) in HCl 1N (45 ml) was cooled on an ice bath. A solution of NaNO2 (0.009 mol) in water (12 ml) was added. The mixture was stirred at 5° C. for 30 min. Ice was added. The mixture was basified with K2CO3 10% and extracted with DCM. The organic, layer was separated, dried (MgSO4), filtered and the solvent was evaporated till dryness. The residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1; 20–45 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from CH3CN/2-propanone/DIPE. The precipitate was filtered off and dried, yielding 1 g (23.2%) of 6-(3-chlorophenyl)-α-(4-chlorophenyl)-α-(1-methyl-1H-imidazol-5-yl)-4H,6H-tetrazolo[1,5-a][4,1]benzothiazepine-8-methanol, mp. 217° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. additionIce was added
  3. extractionextracted with DCM
  4. customThe organic, layer was separated
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated till dryness
  8. customThe residue (5 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 96/4/0.1; 20–45 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from CH3CN/2-propanone/DIPE
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-c7cf41decb234c45a0eb01d3472fb7d0
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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