Methanol → 2-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole

HRID 465774ノート

反応式

HRID 465774 の反応式
[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=2)[C:7]([CH2:11][OH:12])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4].S(=O)(=O)(O)O.[CH3:28]O>>[CH2:1]([C:5]1[N:6]([CH2:13][C:14]2[CH:15]=[CH:16][C:17]([N+:20]([O-:22])=[O:21])=[CH:18][CH:19]=2)[C:7]([CH2:11][O:12][CH3:28])=[C:8]([Cl:10])[N:9]=1)[CH2:2][CH2:3][CH3:4]

参加物

4

反応物 3

HCID 887MethanolHCID 1118Sulfuric AcidHCID 153564431-(4-Nitrobenzyl)-2-butyl-4-chloro-5-hydroxymethyl imidazole

生成物 1

HCID 537649382-n-Butyl-4-chloro-5-methoxymethyl-1-(4-nitrobenzyl)imidazole

実験手順

2-n-butyl-4-chloro-5-hydroxymethyl-1-(4-nitrobenzyl)imidazole (10.5 g, 32.4 mmol, 1 eq), conc. sulfuric acid (26 mL) and methanol (300 mL) were mixed and refluxed overnight. The solvent was removed in vacuo and the residue taken up in water (about 300 mL). The pH was adjusted to 5 with 1N NaOH and then this aqueous portion extracted with ethyl acetate (3× 250 mL). The organic layers were collected, dried (MgSO4) and the solvent removed in vacuo to yield 11.57 g of an amber oil. NMR (200 MHz, CDCl3) δ8.22 (d, 2H, J=8 Hz); 7.15 (d, 2H, J=8 Hz); 5.26 (s, 2H); 4.25 (s, 2H); 3.23 (s, 3H); 2.52 (t, 2H, J=7 Hz); 1.64 (t of t, 2H, J=7,7 Hz); 1.28 (t of q, 2H, J=7,7 Hz); 0.81 (t, 3H, J=7 Hz). Anal. Calcd. for C16H20ClN3O3.(H2O)0.5 : C, 55.41; H, 6.10; Cl, 10.22. Found: C, 55.21; H, 6.22; Cl, 9.92.

後処理

  1. temperaturerefluxed overnight
  2. customThe solvent was removed in vacuo
  3. extractionthis aqueous portion extracted with ethyl acetate (3× 250 mL)
  4. customThe organic layers were collected
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed in vacuo

出典と根拠

ORDレコード
ord-79cfbc3dee044deba9343d14afe98572
出典データセット
uspto-grants-1992_10
特許番号
US05153197

反応ノート

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