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

HRID 1869752ノート

反応式

HRID 1869752 の反応式
[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]

参加物

8

反応物 4

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

生成物 1

HCID 579875492-Azido-4-iodo-1-methylbenzene収率 64%

試薬・触媒・溶媒 3

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒2 回HCID 6344Dichloromethane溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-81e5290b0ae54583ac38c0a36808fb94
出典データセット
uspto-grants-2009_12
特許番号
US07638629B2

反応ノート

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