Sodium Azide → HCID 58971806、化合物

HRID 19457ノート

反応式

HRID 19457 の反応式
[CH2:1]([N:3]([CH2:16][CH3:17])[C:4]1[CH:13]=[C:12]2[C:7]([CH:8]=[C:9]([NH2:15])[C:10](=[O:14])[O:11]2)=[CH:6][CH:5]=1)[CH3:2].N([O-])=O.[Na+].C([O-])(=O)C.[K+].[N-:27]=[N+:28]=[N-].[Na+]>Cl.O>[N:15]([C:9]1[C:10](=[O:14])[O:11][C:12]2[C:7]([CH:8]=1)=[CH:6][CH:5]=[C:4]([N:3]([CH2:1][CH3:2])[CH2:16][CH3:17])[CH:13]=2)=[N+:27]=[N-:28]

参加物

7

反応物 4

HCID 33557Sodium AzideHCID 517044Potassium AcetateHCID 23668193Sodium NitriteHCID 770781653-amino-7-(diethylamino)-2H-chromen-2-one

生成物 1

HCID 58971806HCID 58971806、化合物

試薬・触媒・溶媒 2

HCID 313Hydrochloric Acid溶媒HCID 962Water溶媒

反応条件

温度
2.5 °C

実験手順

7-Diethylamino-3-amino coumarin (100 mg, 0.43 mmol) was dissolved slowly in HCl aq. (17.2%, 4 mL) at room temperature. Upon cooling to 0-5° C. and addition of a solution of NaNO2 (30 mg, 0.43 mmol), the reaction mixture was stirred for 1 hour at 0-5° C. This was followed by the addition of potassium acetate (2 g) in water (5 mL) to adjust the pH of the resulting solution to 4. Sodium azide (57 mg, 0.88 mmol) was added in portions at 0-5° C., the mixture stirred at 0-5° C. for another five hours. The precipitated product was rapidly filtered, washed with ice-cold water (10 mL) and dried under vacuum to yield the final product as a yellow solid: 84 mg, 80%. The product was stored at −20° C. IR (KBr): 2113 (vs), 1710 (s), 1625 (m), 1512 (m); 1H NMR (300 MHz, CDCl3) δ 1.26 (t, J=7.25 Hz, 6H), 3.48 (q, J=7.24 Hz, 4H), 6.50 (s, 1H), 6.70 (d, J=8.04 Hz, 1H), 7.10 (s, 1H), 7.20 (d, J=9.07 Hz, 1H); EI-MS for C13H14N4O2 m/z (MH+): 259.

後処理

  1. stirringthe mixture stirred at 0-5° C. for another five hours
  2. filtrationThe precipitated product was rapidly filtered
  3. washwashed with ice-cold water (10 mL)
  4. customdried under vacuum

出典と根拠

ORDレコード
ord-b8f8640eed484acea750060e4556e29a
出典データセット
uspto-grants-2010_06
特許番号
US07745229B2

反応ノート

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