Sodium Azide → HCID 22106551, compound

HRID 1456313Notes

Reaction equation

HRID 1456313 reaction equation
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([NH2:15])=[CH:11][C:10]=1[F:16])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(C([CH2:26][CH3:27])(CC)C([O-])([O-])[O-])C.[N-:28]=[N+:29]=[N-:30].[Na+].C(=O)(O)[O-].[Na+]>C(O)(=O)C>[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:26]([CH3:27])=[N:30][N:29]=[N:28]2)=[CH:11][C:10]=1[F:16])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 21875354TriethylorthoaceateHCID 219518923-Fluoro-4-phenylmethoxyaniline

Product 1

HCID 22106551HCID 22106551, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

4-Benzyloxy-3-fluoro-phenylamine as a solution in acetic acid (50 ml) was heated to 75° under nitrogen. Triethylorthoacetate (10.3 ml) was added. After a further 45 min at this temperature, sodium azide (7.8 g) was added portionwise. Heating was continued for a further 3 h, the reaction cooled overnight and poured into sodium bicarbonate solution (8%, ca. 500 ml), extracted with dichloromethane (3×100 ml), dried (Na2SO4) and evaporated. The residue was purified by FCC with (dichloromethane/methanol (995:5)) to give the title compound as a solid (4.6 g).

Workup

  1. temperatureHeating
  2. temperaturethe reaction cooled overnight
  3. extractionextracted with dichloromethane (3×100 ml)
  4. dry with materialdried (Na2SO4)
  5. customevaporated
  6. customThe residue was purified by FCC with (dichloromethane/methanol (995:5))

Sources & evidence

ORD record
ord-0d5e5a5e041145d6af8e41b961d6cc49
Source dataset
uspto-grants-1998_12
Patent number
US05843966

Reaction notes

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