Hydrochloric Acid → HCID 69021592, compound

HRID 860800Notes

Reaction equation

HRID 860800 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:19]=[C:18]([NH:20][NH2:21])[CH2:17][S:16][CH:15]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[C:14]=3[CH:29]=2)=[O:9])=[CH:4][CH:3]=1.Cl.[N:31]([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]([C:10]2[CH:11]=[CH:12][C:13]3[N:19]4[N:31]=[N:21][N:20]=[C:18]4[CH2:17][S:16][CH:15]([C:22]4[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[CH:23]=4)[C:14]=3[CH:29]=2)=[O:9])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 69021596HCID 69021596, compound

Product 1

HCID 69021592HCID 69021592, compoundYield 19.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
5 °C

Procedure

Intermediate (30) (0.01125 mol) was cooled on an ice bath. Hydrochloric acid (90 ml) was added. Then a solution of sodium nitrite (0.013 mol) in water (18 ml) was added quickly dropwise. The mixture was stirred at 5° C. for 30 min and at room temperature for 2 hours. Water 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 (6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10; 15–40 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from DCM/DIPE. The precipitate was filtered off and dried, yielding 1 g (19.6%) of (4-chlorophenyl)[6-(3-chlorophenyl)-4H,6H-tetrazolo[1,5-a][4,1]benzothiazepin-8-yl]-methanone (intermediate 31), mp. 212° C.

Workup

  1. extractionextracted with DCM
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated till dryness
  6. customThe residue (6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH 90/10; 15–40 μm)
  7. customThe pure fractions were collected
  8. customthe solvent was evaporated
  9. customThe residue was crystallized from DCM/DIPE
  10. filtrationThe precipitate was filtered off
  11. customdried

Sources & evidence

ORD record
ord-90667aefed0e411a91c864039a2a9a19
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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