Hydrochloric Acid → HCID 69019814, compound

HRID 860788Notes

Reaction equation

HRID 860788 reaction equation
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]3[N:20]=[C:19]([NH:21][NH2:22])[CH2:18][N:17]=[C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[C:15]=3[CH:30]=2)=[O:10])=[CH:5][CH:4]=1.[N:31]([O-])=O.[Na+].C([O-])([O-])=O.[K+].[K+]>O>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([C:9]([C:11]2[CH:12]=[CH:13][C:14]3[N:20]4[N:31]=[N:22][N:21]=[C:19]4[CH2:18][N:17]=[C:16]([C:23]4[CH:28]=[CH:27][CH:26]=[C:25]([Cl:29])[CH:24]=4)[C:15]=3[CH:30]=2)=[O:10])=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 69020578HCID 69020578, compound

Product 1

HCID 69019814HCID 69019814, compoundYield 65.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

HCl 0.5N (30 ml) was cooled. Intermediate (14) (0.00353 mol) was added. The mixture was cooled while stirring vigorously. A solution of sodium nitrite (0.0037 mol) in water (8 ml) was added dropwise. The mixture was stirred at 5° C. for 45 min, 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 (1.6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 100%; 35–70 μm). The pure fractions were collected and the solvent was evaporated. The residue was crystallized from acetonitrile. The precipitate was filtered off, washed with diethyl ether and dried, yielding 1 g (65%) of (4-chlorophenyl)[6-(3-chlorophenyl)-4H-tetrazolo[1,5-a][1,4]benzodiazepin-8-yl]-methanone (intermediate 15), mp. 220° C.

Workup

  1. temperatureThe mixture was cooled
  2. stirringThe mixture was stirred at 5° C. for 45 min
  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 (1.6 g) was purified by column chromatography over silica gel (eluent: CH2Cl2 100%; 35–70 μm)
  9. customThe pure fractions were collected
  10. customthe solvent was evaporated
  11. customThe residue was crystallized from acetonitrile
  12. filtrationThe precipitate was filtered off
  13. washwashed with diethyl ether
  14. customdried

Sources & evidence

ORD record
ord-ac93edf8aea2442387fe64f168f59c74
Source dataset
uspto-grants-2006_12
Patent number
US07153958B2

Reaction notes

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