Nitric Acid → HCID 21082069, compound

HRID 347008Notes

Reaction equation

HRID 347008 reaction equation
N([O-])=O.[Na+].[N+]([O-])(O)=O.[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([C:35]4[CH:40]=[CH:39][C:38]([I:41])=[CH:37][CH:36]=4)([C:28]4[N:32]([CH3:33])[C:31](S)=[N:30][N:29]=4)[OH:27])[CH:24]=3)[N:19]3[N:42]=[N:43][N:44]=[C:18]3[N:17]=2)[CH:13]=[CH:14][CH:15]=1.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.CCOC(C)=O.O>[Cl:9][C:10]1[CH:11]=[C:12]([C:16]2[C:25]3[C:20](=[CH:21][CH:22]=[C:23]([C:26]([C:35]4[CH:40]=[CH:39][C:38]([I:41])=[CH:37][CH:36]=4)([C:28]4[N:32]([CH3:33])[CH:31]=[N:30][N:29]=4)[OH:27])[CH:24]=3)[N:19]3[N:42]=[N:43][N:44]=[C:18]3[N:17]=2)[CH:13]=[CH:14][CH:15]=1

Participants

8

Reactant 4

HCID 944Nitric AcidHCID 11430Potassium CarbonateHCID 23668193Sodium NitriteHCID 178481709HCID 178481709, compound

Product 1

HCID 21082069HCID 21082069, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
5 °C

Procedure

Sodium nitrite (0.0094 mol) was added at 5° C. to a mixture of nitric acid (12 ml) and water (12 ml). A solution of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(5-mercapto-4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanol (0.0094 mol), obtained in Example B27a, in THF (10 ml) was added. The mixture was stirred at 5° C. for 15 minutes and poured out into ice water. EtOAc was added. The mixture was basified with potassium carbonate 10%. The precipitate was filtered, washed with EtOAc and dried under a vacuum, yielding 3.5 g of fraction F1 (63%) of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanol. The filtrate was extracted with EtOAc. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue was crystallized from 2-propanone. The precipitate was filtered off and dried, yielding 1.5 g F2 (27%). This fraction was taken up in water. The mixture was stirred. The precipitate was filtered off and dried, yielding 1.2 g (21%) of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanol, mp. 228° C.

Workup

  1. additionwas added
  2. filtrationThe precipitate was filtered
  3. washwashed with EtOAc
  4. customdried under a vacuum

Sources & evidence

ORD record
ord-6b0dea843cb6408097449e93fa5d88c7
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

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