Sodium Azide → HCID 68692912, compound

HRID 1157797Notes

Reaction equation

HRID 1157797 reaction equation
CS[C:3](=[N:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=1)[N:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1.[N-:24]=[N+:25]=[N-:26].[Na+]>CN(C=O)C.[Hg](Cl)Cl>[N:19]1[CH:20]=[CH:21][CH:22]=[CH:23][C:18]=1[N:17]1[C:3]([N:4]2[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]2)=[N:26][N:25]=[N:24]1

Participants

5

Reactant 2

HCID 33557Sodium AzideHCID 68691865HCID 68691865, compound

Product 1

HCID 68692912HCID 68692912, compoundYield 84.7%

Reagents, catalysts & solvents 2

HCID 24085Mercuric ChlorideCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
25 °C

Procedure

Part C: To a solution of tert-butyl 4-(methylthio(pyridin-2-ylimino)methyl)piperazine-1-carboxylate (12.00 g, 36.0 mmol) in DMF (200 mL) at 25° C. was added sodium azide (11.60 g, 178 mmol), followed by mercury(II)chloride (10.90 g, 40.0 mmol), and the resulting mixture was stirred at 25° C. for 19 d. The mixture then was filtered, and the solids were washed with DMF. The combined filtrate was concentrated under vacuum, and the residue was diluted with ethyl acetate. The resulting mixture was filtered again. The filtrate was washed with water (×3) and brine, dried over anhyd. sodium sulfate, filtered, and concentrated. Column chromatography on silica gel (elution: 0-20% diethyl ether/methylene chloride) to afford tert-butyl 4-(1-(pyridin-2-yl)-1H-tetrazol-5-yl)piperazine-1-carboxylate (10.10 g) as an off-white solid, following crystallization from a mixture of 1-chlorobutane/hexane; Mass Spec.: m/e: 332.11 (M+H)+ [calc'd: 332.17]; 1HNMR (300 MHz, CDCl3) δ 8.57 (m, 1H), 7.94 (m, 1H), 7.79 (d, 1H, J=8 Hz), 7.40 (m, 1H), 3.52 (m, 4H), 3.34 (m, 4H), 1.43 (s, 9H).

Workup

  1. filtrationThe mixture then was filtered
  2. washthe solids were washed with DMF
  3. concentrationThe combined filtrate was concentrated under vacuum
  4. additionthe residue was diluted with ethyl acetate
  5. filtrationThe resulting mixture was filtered again
  6. washThe filtrate was washed with water (×3) and brine
  7. customdried over anhyd
  8. filtrationsodium sulfate, filtered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-2cfb66c28be14092b314b047d56a32b3
Source dataset
uspto-grants-2010_10
Patent number
US07807676B2

Reaction notes

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