Hydrochloric Acid → HCID 69896546, compound

HRID 346976Notes

Reaction equation

HRID 346976 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:21]4[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=4)[C:19]#[N:20])[CH:16]=3)[N:11]=[C:10]([NH:28][NH2:29])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.Cl.C1COCC1.[N:36]([O-])=O.[Na+]>O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[CH:13][CH:14]=[C:15]([CH:18]([C:21]4[CH:26]=[CH:25][C:24]([I:27])=[CH:23][CH:22]=4)[C:19]#[N:20])[CH:16]=3)[N:11]3[N:36]=[N:29][N:28]=[C:10]3[N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 8028TetrahydrofuranHCID 21082026HCID 21082026, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 69896546HCID 69896546, compoundYield 55.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
5 °C

Procedure

Intermediate (41) (0.0121 mol) was added at 5° C. to a mixture of HCl 1N (60 ml) and THF (60 ml). A solution of sodium nitrite (0.0133 mol) in water (20 ml) was added dropwise at 5° C. The mixture was stirred at 5° C. for 1 hour then brought to room temperature, stirred at room temperature for 5 hours, poured out into ice water and extracted with EtOAc. The organic layer was separated, washed with water, dried (MgSO4), filtered and the solvent was evaporated. The residue was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc; 70/30; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 3.8 g (60%) which were crystallized from 2-propanone/CH3CN. The precipitate was filtered off and dried till dryness, yielding 3.5 g (55%) of 5-(3-chlorophenyl)-α-(4-iodophenyl)-tetrazolo[1,5-α]quinazoline-7-acetonitrile (intermediate 42).

Workup

  1. customthen brought to room temperature
  2. stirringstirred at room temperature for 5 hours
  3. extractionextracted with EtOAc
  4. customThe organic layer was separated
  5. washwashed with water
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. customthe solvent was evaporated
  9. customThe residue was purified by column chromatography over silica gel (eluent: cyclohexane/EtOAc; 70/30; 15–40 μm)
  10. customThe pure fractions were collected
  11. customthe solvent was evaporated
  12. customyielding 3.8 g (60%) which
  13. customwere crystallized from 2-propanone/CH3CN
  14. filtrationThe precipitate was filtered off
  15. customdried till dryness

Sources & evidence

ORD record
ord-345d762d02f148438222301f66bf5ab4
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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