Sodium Azide → 4-(Azidomethyl)benzaldehyde

HRID 1509359ノート

反応式

HRID 1509359 の反応式
Br[CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1.[N-:11]=[N+:12]=[N-:13].[Na+]>CN(C=O)C.C(OCC)(=O)C.O>[N:11]([CH2:2][C:3]1[CH:10]=[CH:9][C:6]([CH:7]=[O:8])=[CH:5][CH:4]=1)=[N+:12]=[N-:13]

参加物

6

反応物 2

HCID 33557Sodium AzideHCID 112064214-(Bromomethyl)benzaldehyde

生成物 1

HCID 574448534-(Azidomethyl)benzaldehyde収率 92.2%

試薬・触媒・溶媒 3

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
60 °C

実験手順

Bromide 3 (180 mg, 0.90 mmol) was dissolved in DMF (10 ml). Sodium azide (88 mg, 1.35 mmol) was added. The reaction mixture was then heated at 60° C. for an hour. The reaction mixture was allowed to cool and was dissolve in ethyl acetate (150 ml) and H2O (150 ml). The phases were separated and the organic phase was washed again with water (2×150 ml). The organic phase was dried over sodium sulphate, and evaporated under reduced pressure to yield 4 as an oil (134 mg, 0.83 mmol, 92%). Rf=0.70 (DCM); νmax=2094, 1694, 1607, 1207, 1167, 812, 773 cm−1; 1H NMR (300 MHz, CDCl3) δ=10.02 (s, 1H, CHO), 7.90 (d, 3J(H,H)=7.9 Hz, 2H, ArCH α to CHO), 7.48 (d, 3J(H,H)=7.9 Hz, 2H, ArCH α to CH2N3), 4.45 (s, 2H, CH2N3); 13C NMR (75 MHz, CDCl3) δ=191.6 (CHO), 142.1 (ArCCH2N3), 136.2 (ArCCHO), 130.2 (ArCH α to ArCCHO), 128.4 (ArCH α to ArCCH2N3), 54.2 (CH2N3); HRMS (ESI+): m/z calculated for C8H7N3ONa [M+Na]+: 184.0481, found 184.0497.

後処理

  1. temperatureto cool
  2. customThe phases were separated
  3. washthe organic phase was washed again with water (2×150 ml)
  4. dry with materialThe organic phase was dried over sodium sulphate
  5. customevaporated under reduced pressure

出典と根拠

ORDレコード
ord-57c9054ecca34e719e4decb6b9b6c5b5
出典データセット
uspto-grants-2015_12
特許番号
US09222941B2

反応ノート

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