Tetrahydrofuran → 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

HRID 553345ノート

反応式

HRID 553345 の反応式
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][C:18]#N)=[N:12][O:13][N:14]=1.[H-].[H-].[H-].[H-].[Li+].[Al+3].C1C[O:29]CC1>>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]1[C:11]([NH:15][CH2:16][CH2:17][CH2:18][OH:29])=[N:12][O:13][N:14]=1

参加物

4

反応物 3

HCID 8028Tetrahydrofuran2 回HCID 21226445Aluminium lithium hydrideHCID 1363893133-[4-(1H-Benzoimidazol-2-yl)-furazan-3-ylamino]-propionitrile

生成物 1

HCID 1364137544-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(3-hydroxypropyl)-amine

実験手順

A solution of 4-(1H-benzimidazol-2-yl)-furazan-3-yl-N-(2-cyanoethyl)-amine (0.272 g, 0.947 mmol, Example 6a) in THF (5 ml) is added dropwise at 0° C. to an efficiently stirred suspension of LiAlH4 (0.054 g, 1.42 mmol) in THF (5 ml). After stirring for 16 hours at room temperature the mixture is quenched by careful addition of aqueous saturated solution of sodium sulphate. The suspension is filtered and the filtrate evaporated to dryness. Crystallization by addition of hexane yields the title compound in pure form. 1H-NMR (400 MHz, d6-DMSO): 13.6 (s, 1H); 7.66 (m, 2H); 7.31 (m, 2H); 6.92 (t, 1H); 4.61 (m, 1H); 3.51 (m, 2H); 3.39 (m, 2H); 1.81 (m, 2H).

後処理

  1. customis quenched by careful addition of aqueous saturated solution of sodium sulphate
  2. filtrationThe suspension is filtered
  3. customthe filtrate evaporated to dryness
  4. customCrystallization
  5. additionby addition of hexane

出典と根拠

ORDレコード
ord-dde274e722b0409d87706d81630193ab
出典データセット
uspto-grants-2011_11
特許番号
USRE042890E1

反応ノート

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