Methanesulfonic Acid → (4-chloro-2-propyl-1H-imidazol-5-yl)methanol

HRID 1874875ノート

反応式

HRID 1874875 の反応式
[Cl:1][C:2]1[N:3]=[C:4]([CH2:16][CH2:17][CH3:18])[NH:5][C:6]=1[CH2:7][O:8]CC1C=CC=CC=1.CS(O)(=O)=O.[OH-].[Na+]>C(Cl)(Cl)Cl>[Cl:1][C:2]1[N:3]=[C:4]([CH2:16][CH2:17][CH3:18])[NH:5][C:6]=1[CH2:7][OH:8]

参加物

5

反応物 3

HCID 6395Methanesulfonic AcidHCID 14798Sodium HydroxideHCID 594513894-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole

生成物 1

HCID 10374924(4-chloro-2-propyl-1H-imidazol-5-yl)methanol収率 82%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒

実験手順

A solution of 4-chloro-5-{[(phenylmethyl)oxy]methyl}-2-propyl-1H-imidazole (1.72 g, 6.5 mmol) and methanesulfonic acid (16 mL, 247 mmol) in chloroform (36 mL) was stirred at RT for 1 h. The reaction mixture was poured into ice (˜70 g) and the solution was neutralized by addition of 5N NaOH until the pH was 10. The solution was extracted with methyl tert-butyl ether (2×60 mL) and then with n-butanol (3×40 mL). The combined n-butanol extracts were concentrated, washed with brine, and dried in vacuo to provide the title compound (0.927 g, 82%) as a light yellow solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 12.09 (br. s., 1H), 5.10 (br. s., 1H), 4.31 (s, 2H), 2.45-2.51 (m, 2H), 1.60 (sex, 2H), 0.87 (t, 3H).

後処理

  1. extractionThe solution was extracted with methyl tert-butyl ether (2×60 mL)
  2. concentrationThe combined n-butanol extracts were concentrated
  3. washwashed with brine
  4. customdried in vacuo

出典と根拠

ORDレコード
ord-4fe9f3c5e8a54e7d8f1da7be70a7fa81
出典データセット
uspto-grants-2012_11
特許番号
US08304419B2

反応ノート

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