Nitric Acid → HCID 23338150, compound

HRID 347004Notes

Reaction equation

HRID 347004 reaction equation
N([O-])=O.[Na+].[N+]([O-])(O)=O.ClC1C=C([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23](C(C4C=CC(I)=CC=4)C4N(C)C(S)=NN=4)[CH:24]=3)[N:19]3[N:41]=[N:42][N:43]=[C:18]3[N:17]=2)C=CC=1.CCOC(C)=O>O.C1COCC1>[N:41]1[N:19]2[C:20]3[C:25]([CH:16]=[N:17][C:18]2=[N:43][N:42]=1)=[CH:24][CH:23]=[CH:22][CH:21]=3

Participants

7

Reactant 4

HCID 944Nitric AcidHCID 8857Ethyl AcetateHCID 23668193Sodium NitriteHCID 178481699HCID 178481699, compound

Product 1

HCID 23338150HCID 23338150, compoundYield 140.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
5 °C

Procedure

Sodium nitrite (0.0005 mol) was added at 5° C. to a solution of nitric acid (1 ml) in water (1 ml) A solution of 5-[[5-(3-chlorophenyl)tetrazolo[1,5-a]quinazolin-7-yl](4-iodophenyl)methyl]-4-methyl-4H-1,2,4-triazole-3-thiol (0.0005 mol), obtained in stage a), in THF (2 ml) was added dropwise. The mixture was stirred at 5° C. for 15 minutes and poured out into ice water. EtOAc was added. The mixture was washed with potassium carbonate 10%. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (0.23 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1;15–40 μm). The pure fractions were collected and the solvent was evaporated., yielding 0.12 g (44%) of tetrazolo[1,5-a]quinazoline, 5-(3-chlorophenyl)-7-[(4-iodophenyl)(4methyl-4H-1,2,4-triazol-3-yl)methyl]-, mp. 150° C.

Workup

  1. additionwas added dropwise
  2. washThe mixture was washed with potassium carbonate 10%
  3. customThe organic layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customthe solvent was evaporated
  7. customThe residue (0.23 g) was purified by column chromatography over silica gel (eluent: CH2Cl2/CH3OH/NH4OH 97/3/0.1;15–40 μm)
  8. customThe pure fractions were collected
  9. customthe solvent was evaporated

Sources & evidence

ORD record
ord-346a1082badc44a2aead657dae0cac37
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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