Ammonium Chloride → HCID 178422719, compound

HRID 1902529Notes

Reaction equation

HRID 1902529 reaction equation
[C:1]([CH2:3][CH2:4][N:5]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[C:7]([CH2:14][C:15]2[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=2)=[C:6]1[CH3:21])#[N:2].[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C)C=O>[NH:22]1[C:1]([CH2:3][CH2:4][N:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7]([CH2:14][C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)=[C:6]2[CH3:21])=[N:2][N:24]=[N:23]1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 20515679HCID 20515679, compound

Product 1

HCID 178422719HCID 178422719, compoundYield 21.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

A mixture of 1-(2-cyanoethyl)-2-methyl-3-(3-pyridylmethyl)indole (0.8 g), sodium azide (0.95 g), ammonium chloride (0.78 g) and dry dimethylformamide (12 ml) was heated with stirring at 125° C. for 20 hours and then evaporated. Water (25 ml) was added to the residue to dissolve inorganic material. The insoluble portion was crystallised from methanol/ethyl acetate to give 1-[2-(5-tetrazolyl)ethyl]-2-methyl-3-(3-pyridylmethyl)indole (0.20 g), m.p. 173°.

Workup

  1. temperaturewas heated
  2. customevaporated
  3. additionWater (25 ml) was added to the residue
  4. dissolutionto dissolve inorganic material
  5. customThe insoluble portion was crystallised from methanol/ethyl acetate

Sources & evidence

ORD record
ord-e215f75e3b0d481394a0c49e26281d8f
Source dataset
uspto-grants-1982_12
Patent number
US04363912

Reaction notes

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