Benzyl Bromide → 1-Benzyl-5,6-dichloro-1H-benzimidazole-2-amine

HRID 263896

反応式

HRID 263896 の反応式
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].[CH2:15](Br)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1>C(#N)C>[NH2:1][C:2]1[N:3]([CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:4]2[CH:10]=[C:9]([Cl:11])[C:8]([Cl:12])=[CH:7][C:5]=2[N:6]=1

参加物

5

反応物 3

HCID 7498Benzyl BromideHCID 14798Sodium HydroxideHCID 4660162-Amino-5,6-dichlorobenzimidazole

生成物 1

HCID 105655441-Benzyl-5,6-dichloro-1H-benzimidazole-2-amine収率 85.1%

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

実験手順

2-Amino-5,6-dichlorobenzimidazole (4) (1 g, 4.95 mmole) was dissolved in acetonitrile (200 ml) and NaOH (198 mg, 4.95 mmole) was added. After stirring for 1 hr at room temperature, benzyl bromide (0.589 ml, 4.95 mmole) was added and the mixture was allowed to stir overnight. The mixture was concentrated under reduced pressure and purified on a silica gel column (3.5×5 cm) using 5% MeOH/CHCl3 to give 1.23 g (85%) of 2-amino-1-benzyl-5,6-dichlorobenzimidazole (182). The compound was then recrystallized from EtOH/H2O to give a white powder. 1H NMR (DMSO-d6): d 5.28 ppm (s, 2H), 6.95 (s, 2H), 7.16 (d, 2H), 7.25 (d, 1H), 7.31 (m, 4H). 13C NMR (DMSO-d6): d 44.74 ppm, 109.15, 115.37, 119.62, 122.66, 126.82, 127.37, 128.55, 134.10, 136.46, 143.13, 156.91. MS (Electron Impact): m/e 291, 200, 158, 91, 65. MP: 245°-246° C. Elemental Analysis: (C14H11Cl2N3,): Calculated: C, 57.55; H, 3.79; N, 14.38. Found: C, 57.66; H, 3.83; N, 13.98. UV imax nm (e×104): (pH 7) 230 (0.761), 260 (0.324), 302 (0.452); (pH 1) 238 (0.306), 294 (0.383), 299 (0.359); (pH 11) 229 (0.869), 257 (0.316), 301 (0.443).

後処理

  1. stirringto stir overnight
  2. concentrationThe mixture was concentrated under reduced pressure
  3. custompurified on a silica gel column (3.5×5 cm)

出典と根拠

ORDレコード
ord-6625eb9909744dd8a86359c8df7c2067
出典データセット
uspto-grants-1997_07
特許番号
US05646125

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