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

HRID 1030576

반응식

HRID 1030576 반응식
[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

참가 물질

5

반응물 3

HCID 5874259Neryl chlorideHCID 23719242Sodium hydroxide--water (1/1/1)HCID 178527775HCID 178527775, 화합물

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-a55c77ed868b499299a96a94630496ec
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05106863

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