Sodium Azide → HCID 60207713, compound

HRID 1776134Notes

Reaction equation

HRID 1776134 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])=[O:8].[N-:19]=[N+:20]=[N-:21].[Na+]>CN(C=O)C>[N:19]([CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][C:7]([NH:9][C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=1[N+:16]([O-:18])=[O:17])=[O:8])=[N+:20]=[N-:21]

Participants

4

Reactant 2

HCID 33557Sodium AzideHCID 60207712HCID 60207712, compound

Product 1

HCID 60207713HCID 60207713, compoundYield 90.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2 (28.4 g, 90 mmol) and sodium azide (12 g, 184 mmol) in DMF (200 mL) was stirred overnight at room temperature. The reaction mixture was poured into ice-water (500 mL) and extracted with ethyl acetate (2×200 mL). The combined organic phase was washed with water (4×100 mL) and brine (50 mL). After removal of the solvent the crude product was passed through a silica gel pad (100 g) and washed with 1:2 mixture of hexane and diethyl ether. Concentration of the appropriate fractions gave 22.5 g of 3 as a pale yellow oil. LC-MS (M++Na) 300

Workup

  1. extractionextracted with ethyl acetate (2×200 mL)
  2. washThe combined organic phase was washed with water (4×100 mL) and brine (50 mL)
  3. customAfter removal of the solvent the crude product
  4. washwashed with 1:2 mixture of hexane and diethyl ether

Sources & evidence

ORD record
ord-b1796a239b9c41ca90bd253e0000627e
Source dataset
uspto-grants-2016_02
Patent number
US09265734B2

Reaction notes

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