Water → HCID 19600386, compound

HRID 609761Notes

Reaction equation

HRID 609761 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[CH:7]2)([O-:3])=[O:2].[H-].[Na+].Cl[CH2:16][C:17]1[N:21]([CH:22]([CH3:24])[CH3:23])[N:20]=[N:19][N:18]=1.O>CN(C)C=O.ClCCl>[CH:22]([N:21]1[C:17]([CH2:16][N:9]2[C:10]3[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=3)[CH:7]=[CH:8]2)=[N:18][N:19]=[N:20]1)([CH3:24])[CH3:23]

Participants

7

Reactant 4

HCID 962WaterHCID 225235-NitroindoleHCID 24758Sodium hydrideHCID 19600396HCID 19600396, compound

Product 1

HCID 19600386HCID 19600386, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
60 °C

Procedure

1.5 Grams of 5-nitroindole was dissolved in 70 ml of dimethylformamide, then 370 mg of sodium hydride (in oil) was added thereto, the mixture was stirred under nitrogen gas stream at 60° C. for 1 hour. Under cooling at 0° C., 1.63 g of 5-chloromethyl-1-isopropyl-1,2,3,4-tetrazole was added, the reaction mixture was stirred at room temperature for 4.5 hours. After the reaction was finished, water was added to the reaction mixture, then the separated crystals were collected by filtration and washed with water. The crystals were dissolved in dichloromethane, the solution was dried with anhydrous magnesium sulfate, and the solvent was removed by distillation under reduced pressure. The residue obtained was subjected to a silica gel column chromatography (eluent: dichloromethane→3% methanol/dichloromethane), there was obtained 2.3 g of 1-(1-isopropyl-1,2,3,4-tetrazol-5-ylmethyl)-5-nitroindole as in the form of yellow powder.

Workup

  1. temperatureUnder cooling at 0° C.
  2. stirringthe reaction mixture was stirred at room temperature for 4.5 hours
  3. filtrationthe separated crystals were collected by filtration
  4. washwashed with water
  5. dissolutionThe crystals were dissolved in dichloromethane
  6. dry with materialthe solution was dried with anhydrous magnesium sulfate
  7. customthe solvent was removed by distillation under reduced pressure
  8. customThe residue obtained

Sources & evidence

ORD record
ord-35fa088cec7e497bb5314397a1ef67e4
Source dataset
uspto-grants-1999_12
Patent number
US05998437

Reaction notes

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