Hydrochloric Acid → HCID 19976993, compound

HRID 1450517Notes

Reaction equation

HRID 1450517 reaction equation
[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([NH2:8])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].Cl.[N:12]([O-])=O.[Na+].C1(S([NH:25][N:26]=[CH:27][C:28]2[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=2)(=O)=O)C=CC=CC=1>O.N1C=CC=CC=1.C(O)C>[CH:1]([C:4]1[CH:10]=[CH:9][C:7]([N:8]2[N:25]=[N:26][C:27]([C:28]3[CH:33]=[CH:32][C:31]([O:34][CH3:35])=[CH:30][CH:29]=3)=[N:12]2)=[CH:6][CH:5]=1)([CH3:3])[CH3:2]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 74644-IsopropylanilineHCID 360809HCID 360809, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19976993HCID 19976993, compoundYield 54.4%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 1049PyridineSolvent

Procedure

4-Isopropylaniline (1.35 g) was added to a mixed solution of 50% ethanol (16 ml) and concentrated hydrochloric acid (2.6 ml). To the mixture was added a solution of sodium nitrite (0.69 g) in water (4 ml) over 10 min below 5° C. and stirring was continued for 10 min. To a solution of 4-methoxybenzaldehyde phenylsulfonylhydrazone (2.9 g) in pyridine (60 ml) was added dropwise the above solution of diazonium salt during 20 min at -10° C.~-15° C., and stirring was continued for 30 min at -10° C. and for 30 min at room temperature. The mixture was poured into ice water and extracted with ethyl acetate. The extract was washed succesively with 4 N hydrochloric acid, water, aqueous sodium carbonate,and water, dried, and evaporated to dryness. The residue was purified by column chromatography on silica gel with benzene-hexane (1/2-2/1) as an eluate to give 2-(4-isopropylphenyl)-5-(4-methoxyphenyl)tetrazole (1.6 g,54%). To a solution of 2-(4- isopropylphenyl)-5-(4-methoxyphenyl)tetrazole (1.3 g) in dichloromethane (10 ml) was added dropwise boron tribromide (10 ml,2.6M solution in dichloromethane) at -10° C. Stirring was continued for 1 h at -10° C. and for 1 h at room temperature. To the mixture was added water (20 ml), and the mixture was extracted with chloroform. The extract was washed with water, dried and evaporated to dryness. The residue was recrystallized from benzene to give 1.1 g (72%) of the title compound.

Workup

  1. stirringstirring
  2. waitwas continued for 30 min at -10° C. and for 30 min at room temperature
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed succesively with 4 N hydrochloric acid, water, aqueous sodium carbonate,and water
  5. customdried
  6. customevaporated to dryness
  7. customThe residue was purified by column chromatography on silica gel with benzene-hexane (1/2-2/1) as an eluate

Sources & evidence

ORD record
ord-76f5808f21ab41b19157a2dfc31f1451
Source dataset
uspto-grants-1997_02
Patent number
US05602161

Reaction notes

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