Sodium Azide → 4-Azido-5-iodo-2-methoxybenzoic acid

HRID 1872686Notes

Reaction equation

HRID 1872686 reaction equation
[NH2:1][C:2]1[C:10]([I:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1.N([O-])=O.[Na+].[N-:18]=[N+:19]=[N-].[Na+]>FC(F)(F)C(O)=O.O>[N:1]([C:2]1[C:10]([I:11])=[CH:9][C:5]([C:6]([OH:8])=[O:7])=[C:4]([O:12][CH3:13])[CH:3]=1)=[N+:18]=[N-:19]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 153457254-Amino-5-iodo-2-methoxybenzoic acidHCID 23668193Sodium Nitrite

Product 1

HCID 186873664-Azido-5-iodo-2-methoxybenzoic acidYield 84.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 4-amino-5-iodo-2-methoxybenzoic acid (300 mg, 1.02 mmol) in trifluoroacetic acid (4 ml) at 5° C., was added sodium nitrite (283 mg, 4.1 mmol) portionwise, and the mixture allowed to stir for 30 min. Sodium azide (200 mg, 3.07 mmol) was then added portionwise and the mixture stirred for a further 30 min at 0° C. The mixture was diluted with water, and a yellow solid precipithated. The solid was filtered, washed with cold water and dried, to afford the title compound (274 mg, 84%).

Workup

  1. stirringthe mixture stirred for a further 30 min at 0° C
  2. filtrationThe solid was filtered
  3. washwashed with cold water
  4. customdried

Sources & evidence

ORD record
ord-c73db79b26e746e5918b2a329a71343b
Source dataset
uspto-grants-2000_08
Patent number
US06110934

Reaction notes

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