Neryl chloride → 2-[(3,7-Dimethyl-2,6(Z)-octadienyl)-thio]-1H-1,3-benzimidazole

HRID 1030576

反応式

HRID 1030576 の反応式
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[Na+].O.[CH2:14](Cl)/[CH:15]=[C:16](\[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])/[CH3:17]>CO>[CH3:17]/[C:16](/[CH2:18][CH2:19][CH:20]=[C:21]([CH3:23])[CH3:22])=[CH:15]/[CH2:14][S:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

参加物

5

反応物 3

HCID 5874259Neryl chlorideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178527775HCID 178527775、化合物

生成物 1

HCID 867457032-[(3,7-Dimethyl-2,6(Z)-octadienyl)-thio]-1H-1,3-benzimidazole

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

To a solution of 2-mercaptobenzimidazole (5.1 g, 34 mmol) and 2N NaOH/H2O (pH 11) in methanol (100 mL) was added neryl chloride (5.85 g, 34 mmol). The reaction mixture was stirred at ambient temperature for 16 hours, evaporated in vacuo, dissolved in CH2Cl2, washed with saturated NaHCO3 and brine, and dried over Na2SO4. Evaporation of the solvent gave an oil which was flash chromatographed (Merck Kieselgel, 5% MeOH/CH2Cl2) to give the title compound which was crystallized from Et2O/pentane to give a white solid (3.4 g, 35%). m.p. 98°-101° C. NMR (CDCl3)δ7.35(m 4H) 5.25(m 2H) 4.0(d,J=6 Hz,2H), 2.05(m,4H), 1.68(s,3H), 1.62(s,3H), 1.60(s,3H).

後処理

  1. customevaporated in vacuo
  2. dissolutiondissolved in CH2Cl2
  3. washwashed with saturated NaHCO3 and brine
  4. dry with materialdried over Na2SO4
  5. customEvaporation of the solvent
  6. customgave an oil which
  7. customchromatographed (Merck Kieselgel, 5% MeOH/CH2Cl2)

出典と根拠

ORDレコード
ord-a55c77ed868b499299a96a94630496ec
出典データセット
uspto-grants-1992_04
特許番号
US05106863

関連ノート

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