Hydrochloric Acid → HCID 178497410, compound

HRID 399833Notes

Reaction equation

HRID 399833 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([N:13]2[CH:17]=[CH:16][CH:15]=[CH:14]2)[CH:6]=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])#[N:2].[N-:18]=[N+:19]=[N-:20].[Na+].[Cl-].[NH4+].N([O-])=O.[Na+].Cl>CN(C)C=O>[N:13]1([C:5]2[CH:6]=[C:7]([CH:12]=[C:3]([C:1]3[NH:20][N:19]=[N:18][N:2]=3)[CH:4]=2)[C:8]([O:10][CH3:11])=[O:9])[CH:17]=[CH:16][CH:15]=[CH:14]1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 18945363HCID 18945363, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 178497410HCID 178497410, compoundYield 93.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture of methyl 5-cyano-3-(pyrrol-1-yl)benzoate (3.0 g), sodium azide (5.2 g) and ammonium chloride (4.3 g) in N,N-dimethylformamide (12 ml) was stirred for 4 hours at 120°-125° C. The mixture was added to the ice-water (100 ml) and to the mixture was added sodium nitrite (5.5 g). The mixture was adjusted to pH 1 with 6N-hydrochloric acid and stirred for 30 minutes. The mixture was extracted with ethyl acetate. The extract layer was washed with brine and dried over magnesium sulfate. The solvent was removed by concentration and the residue was triturated with diisopropyl ether to give methyl 3-(pyrrol-1-yl)-5-(1H-tetrazol-5-yl)benzoate (3.35 g).

Workup

  1. stirringstirred for 30 minutes
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe extract layer was washed with brine
  4. dry with materialdried over magnesium sulfate
  5. customThe solvent was removed by concentration
  6. customthe residue was triturated with diisopropyl ether

Sources & evidence

ORD record
ord-779e11fd9e3047abb4510d870caf0f03
Source dataset
uspto-grants-1998_10
Patent number
US05824691

Reaction notes

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