Sodium Azide → HCID 57577557, compound

HRID 13230Notes

Reaction equation

HRID 13230 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][NH2:10])[CH:5]=[CH:4][C:3]=1[OH:11].N([O-])=O.[Na+].[N-:16]=[N+:17]=[N-].[Na+]>Cl.O>[NH2:10][CH2:9][CH2:8][C:6]1[CH:5]=[CH:4][C:3]([OH:11])=[C:2]([N:1]=[N+:16]=[N-:17])[CH:7]=1

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 1337433-AminotyramineHCID 23668193Sodium Nitrite

Product 1

HCID 57577557HCID 57577557, compound

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×

Conditions

Temperature
0 °C

Procedure

2-Amino-4-(2-amino-ethyl)-phenol (1) (1 mmol) is dissolved in aqueous HCl. The solution is cooled to 0° C. and 1 mmol of NaNO2 dissolved in H2O is added slowly with stirring. The reaction mixture is maintained at 0° C. for 1 hr, then NaN3 (2 mmol) dissolved in water is added dropwise with stirring. The resulting mixture is maintained at 0° C. for 1 hr, then the cooling bath is removed and the mixture stirred overnight at ambient temperature. The product is extracted with ethyl acetate, washed with saturated NaHCO3 and H2O. The organic phase is dried with Na2SO4, then the solvent removed under vacuum. The crude product is purified by column chromatography to yield 4-(2-amino-ethyl)-2-azido-phenol (2).

Workup

  1. additionis added slowly
  2. temperatureThe reaction mixture is maintained at 0° C. for 1 hr
  3. additionis added dropwise
  4. stirringwith stirring
  5. temperatureThe resulting mixture is maintained at 0° C. for 1 hr
  6. customthe cooling bath is removed
  7. stirringthe mixture stirred overnight at ambient temperature
  8. extractionThe product is extracted with ethyl acetate
  9. washwashed with saturated NaHCO3 and H2O
  10. dry with materialThe organic phase is dried with Na2SO4
  11. customthe solvent removed under vacuum
  12. customThe crude product is purified by column chromatography

Sources & evidence

ORD record
ord-c5b11a03869340b693cb8898b24dfdd4
Source dataset
uspto-grants-2010_06
Patent number
US07728051B2

Reaction notes

Loading…