2-Propanol, reaction products with ammonia, distn. residues → HCID 21082068, compound

HRID 347010Notes

Reaction equation

HRID 347010 reaction equation
[NH3:1].CC(O)C.Cl[C:7]([C:34]1[CH:39]=[CH:38][C:37]([I:40])=[CH:36][CH:35]=1)([C:28]1[N:32]([CH3:33])[CH:31]=[N:30][N:29]=1)[C:8]1[CH:9]=[C:10]2[C:15](=[CH:16][CH:17]=1)[N:14]1[N:18]=[N:19][N:20]=[C:13]1[N:12]=[C:11]2[C:21]1[CH:26]=[CH:25][CH:24]=[C:23]([Cl:27])[CH:22]=1>C1COCC1>[Cl:27][C:23]1[CH:22]=[C:21]([C:11]2[C:10]3[C:15](=[CH:16][CH:17]=[C:8]([C:7]([C:34]4[CH:35]=[CH:36][C:37]([I:40])=[CH:38][CH:39]=4)([C:28]4[N:32]([CH3:33])[CH:31]=[N:30][N:29]=4)[NH2:1])[CH:9]=3)[N:14]3[N:18]=[N:19][N:20]=[C:13]3[N:12]=2)[CH:26]=[CH:25][CH:24]=1

Participants

4

Reactant 2

HCID 183319422-Propanol, reaction products with ammonia, distn. residuesHCID 21082086HCID 21082086, compound

Product 1

HCID 21082068HCID 21082068, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

NH3/iPrOH (45 ml) was added dropwise at 5° C. to a mixture of 7-[chloro(4-iodophenyl)(4-methyl-4H-1,2,4-triazol-3-yl)methyl]-5-(3-chlorophenyl)-tetrazolo[1,5-a]quinazoline (0.0076 mol) in THF (45 ml). The mixture was brought to room temperature, poured out into a pressure vessel, stirred at 60° C. for 6 hours, cooled and poured out into ice water. The precipitate was filtered off and dried under a vacuum, yielding 1.6 g of a first batch of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine (35%) The aqueous layer was extracted with DCM. The organic layer was separated, dried (MgSO4), filtered, and the solvent was evaporated. The residue (1.7 g) was purified by column chromatography over silica gel (eluent: toluene/iPrOH/NH4OH 84/15/1; 15–40 μm). The pure fractions were collected and the solvent was evaporated, yielding 1.03 g (23%) of a second batch of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine. A sample (0.23 g) was crystallized from CH3CN, the precipitate was filtrated and dried yielding 0.09 g of 5-(3-chlorophenyl)-α-(4-iodophenyl)-α-(4-methyl-4H-1,2,4-triazol-3-yl)-tetrazolo[1,5-a]quinazoline-7-methanamine, mp. 238° C.

Workup

  1. customwas brought to room temperature
  2. additionpoured out into a pressure vessel
  3. temperaturecooled
  4. filtrationThe precipitate was filtered off
  5. customdried under a vacuum

Sources & evidence

ORD record
ord-e4c6a84a1022468cbe61c7d599513be4
Source dataset
uspto-grants-2007_02
Patent number
US07173040B2

Reaction notes

Loading…