Sodium Azide → HCID 22612300, compound

HRID 843988Notes

Reaction equation

HRID 843988 reaction equation
[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([NH2:15])[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH:16]([O-])([O-])OCC.[N-:22]=[N+:23]=[N-:24].[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[C:11]([N:15]2[CH:16]=[N:24][N:23]=[N:22]2)[CH:12]=[CH:13][CH:14]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 33557Sodium AzideHCID 928923-BenzyloxyanilineHCID 53630039Ethylorthoformate

Product 1

HCID 22612300HCID 22612300, compoundYield 34.2%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent2×

Procedure

To a solution of 3-Benzyloxy-phenylamine (1.50 grams, 7.53 mmole) and acetic acid (15 ml) at 70° C. was added a solution of ethyl orthoformate (1.116 g, 7.53 mmole) in acetic acid (4 ml) and stirred for 4 hours. To the solution was added sodium azide (1.468 g, 22.6 mmole) in two portions and stirred for 20 hours at 70° C. The mixture was extracted with ethyl acetate. The combined extracts were washed with saturated sodium hydrogencarbonate and brine, dried over Na2SO4, filtered, and concentrated. The product was purified via flash chromatography on silica using 3/1 hexane/ethyl acetate as eluent to give white crystals (0.650 g). M.P. 85-86° C.; MW 252.25; MS (m/e) 252.8 (M+).

Workup

  1. stirringstirred for 20 hours at 70° C
  2. extractionThe mixture was extracted with ethyl acetate
  3. washThe combined extracts were washed with saturated sodium hydrogencarbonate and brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe product was purified via flash chromatography on silica using 3/1 hexane/ethyl acetate as eluent

Sources & evidence

ORD record
ord-e03734aef48e46cc8d69ab7106545b67
Source dataset
uspto-grants-2002_04
Patent number
US06380218B1

Reaction notes

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