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

HRID 1869752노트

반응식

HRID 1869752 반응식
[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]

참가 물질

8

반응물 4

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

생성물 1

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

시약·촉매·용매 3

HCID 313Hydrochloric Acid용매HCID 962Water용매2회HCID 6344Dichloromethane용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-81e5290b0ae54583ac38c0a36808fb94
출처 데이터셋
uspto-grants-2009_12
특허 번호
US07638629B2

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