Sodium Carbonate → 2-Azido-4-iodo-1-methylbenzene

HRID 1869752Notes

Reaction equation

HRID 1869752 reaction equation
[I:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:9])=[C:6]([CH:8]=1)[NH2:7].N([O-])=O.[Na+].[N-:14]=[N+:15]=[N-].[Na+].C([O-])([O-])=O.[Na+].[Na+]>Cl.O.C(Cl)Cl>[N:7]([C:6]1[CH:8]=[C:2]([I:1])[CH:3]=[CH:4][C:5]=1[CH3:9])=[N+:14]=[N-:15]

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 33557Sodium AzideHCID 5228025-Iodo-o-toluidineHCID 23668193Sodium Nitrite

Product 1

HCID 579875492-Azido-4-iodo-1-methylbenzeneYield 64%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolvent

Procedure

A cold (0° C.) suspension of 5-iodo-2-methylaniline (7.0 g, 0.03M) in HCl (5M, 30 ml) was treated dropwise with a solution of sodium nitrite (2.28 g, 0.033 mmol) in water (3 ml) over 20 minutes. The solution was stirred for 20 minutes before sodium azide was added portionwise over 15 minutes. The mixture was stirred for 30 minutes then poured into water. The mixture was diluted with DCM and the pH adjusted to 7 by the addition of Na2CO3. The phases were separated and the organic layer was dried (MgSO4) and concentrated under vacuum. The residue was purified by chromatography (silica, 5% Et2O/hexanes followed by 10% EtOAc/Hexanes) to give the azide (5.1 g, 64%). 1H NMR (500 MHz, CDCl3): δ 2.14 (3H, s), 6.88 (1H, d, J 7.9), 7.35 (1H, d, J 7.9), 7.39 (1H, d, J 1.3).

Workup

  1. additionwas added portionwise over 15 minutes
  2. customThe phases were separated
  3. dry with materialthe organic layer was dried (MgSO4)
  4. concentrationconcentrated under vacuum
  5. customThe residue was purified by chromatography (silica, 5% Et2O/hexanes followed by 10% EtOAc/Hexanes)

Sources & evidence

ORD record
ord-81e5290b0ae54583ac38c0a36808fb94
Source dataset
uspto-grants-2009_12
Patent number
US07638629B2

Reaction notes

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