Potassium Carbonate → HCID 10118776, compound

HRID 860814Notes

Reaction equation

HRID 860814 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]2[C:14]3[CH:15]=[C:16]([CH:19]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)[C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[CH:17]=[CH:18][C:13]=3[N:12]=[C:11]([NH:33][NH2:34])[CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1.[N:35]([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]([CH:19]([C:26]4[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][CH:27]=4)[C:20]4[N:24]([CH3:25])[CH:23]=[N:22][CH:21]=4)[CH:17]=[CH:18][C:13]=3[N:12]3[N:35]=[N:34][N:33]=[C:11]3[CH2:10][S:9]2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 69021734HCID 69021734, compound

Product 1

HCID 10118776HCID 10118776, compoundYield 18.9%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of 5-(3-chlorophenyl)-7-[(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-2-hydrazino-3,5-dihydro-4,1-benzothiazepine (described in Example B16b) (0.0045 mol) in HCl (34 ml) was cooled on an ice bath. A solution of sodium nitrite (0.005 mol) in water (7 ml) was added. The mixture was stirred at 5° C. for 30 min and at room temperature for 30 min, then poured out on ice, 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 (2.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 20–45 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from 2-propanone/CH3CN/DIPE. The precipitate was filtered off and dried, yielding 0.44 g (18.9%) of 6-(3-chlorophenyl)-8-[(4-chlorophenyl)(1-methyl-1H-imidazol-5-yl)methyl]-4H,6H-tetrazolo[1,5-a][4,1]benzothiazepine, mp. 162° C.

Workup

  1. temperaturewas cooled on an ice bath
  2. additionpoured out on ice
  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 (2.7 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1; 20–45 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from 2-propanone/CH3CN/DIPE
  12. filtrationThe precipitate was filtered off
  13. customdried

Sources & evidence

ORD record
ord-cfda0b27b3324d3888987ed36894d56e
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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