Formaldehyde → 2,5-bis-(hydroxymethyl)-N-benzylimidazole

HRID 8907

反応式

HRID 8907 の反応式
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:13]=[O:14].[C:15]([O-:18])(=O)C.[Na+]>C(O)(=O)C>[OH:14][CH2:13][C:9]1[N:8]([CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)[C:12]([CH2:15][OH:18])=[CH:11][N:10]=1

参加物

5

反応物 3

HCID 712FormaldehydeHCID 779181-BenzylimidazoleHCID 517045Sodium Acetate

生成物 1

HCID 143167542,5-bis-(hydroxymethyl)-N-benzylimidazole収率 24%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

実験手順

Using the procedure of S. Zimmerman et al. (S. C. Zimmerman, K. D. Cramer and A. A. Galan J. Org. Chem. 1989, 54, 1256–1264) N-Benzylimidazole (15 g, 95 mmol) was treated with formaldehyde (60 mL of a 37% aqueous solution), to which glacial acetic acid (8 mL) and sodium acetate (10.5 g) were added. The resulting mixture was stirred until homogeneous, then was transferred to a thick-walled glass tube, which was sealed and placed in a 140° C. oil bath for 12 hours. The tube was then cooled, concentrated, made basic with 10N NaOH, and extracted twice with a 10:1 isopropanol:chloroform mixture. The combined organic fractions were then dried over anhydrous sodium sulfate and concentrated. Purification by chromatography on silica gel (7% methanol in dichloromethane) gave 2,5-bis-(hydroxymethyl)-N-benzylimidazole as a white crystalline solid (4.9 g, 24%). 1H NMR (CDCl3) δ 4.41 (s, 2H), 4.48 (s, 2H), 5.36 (s, 2H), 6.77 (s, 1H), 7.00 (m, 2H), 7.28 (m, 3H).

後処理

  1. additionwere added
  2. customthen was transferred to a thick-walled glass tube
  3. customwhich was sealed
  4. customplaced in a 140° C.
  5. customfor 12 hours
  6. temperatureThe tube was then cooled
  7. concentrationconcentrated
  8. extractionextracted twice with a 10:1 isopropanol
  9. dry with materialThe combined organic fractions were then dried over anhydrous sodium sulfate
  10. concentrationconcentrated
  11. customPurification by chromatography on silica gel (7% methanol in dichloromethane)

出典と根拠

ORDレコード
ord-88763c2edb2b443a865dc1b2c91ebe21
出典データセット
uspto-grants-2006_08
特許番号
US07091217B2

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