Water → HCID 11446587, compound

HRID 1484201Notes

Reaction equation

HRID 1484201 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8].[N-:11]=[N+:12]=[N-:13].[Na+].O>CN(C=O)C>[N:11]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([O:9][CH3:10])=[O:8])=[N+:12]=[N-:13]

Participants

5

Reactant 3

HCID 962WaterHCID 33557Sodium AzideHCID 4170292Methyl 6-Bromohexanoate

Product 1

HCID 11446587HCID 11446587, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
75 °C

Procedure

Methyl 6-azidohexanoate was synthesized via a modified literature procedure. A reaction mixture of methyl 6-bromohexanoate (6 g, 29 mmol) and NaN3 (9.4 g, 144 mmol) in 30 ml of DMF was stirred at 75° C. for 14 h under N2. After cooling down, the reaction mixture was poured into water. The product was extracted with hexane, washed with brine, and dried under MgSO4. Solvent was evaporated to give transparent liquid. Yield: 95%.

Workup

  1. temperatureAfter cooling down
  2. extractionThe product was extracted with hexane
  3. washwashed with brine
  4. customdried under MgSO4
  5. customSolvent was evaporated
  6. customto give transparent liquid

Sources & evidence

ORD record
ord-035d3fd998db48e881d9c154c5db446e
Source dataset
uspto-grants-2016_08
Patent number
US09421276B2

Reaction notes

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