Dimethyl Sulfoxide → 1-Benzyl-5-nitro-1H-indole

HRID 566376노트

반응식

HRID 566376 반응식
CS(C)=O.[OH-].[K+].[N+:7]([C:10]1[CH:11]=[C:12]2[C:16](=[CH:17][CH:18]=1)[NH:15][CH:14]=[CH:13]2)([O-:9])=[O:8].[CH2:19](Br)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>O>[CH2:19]([N:15]1[C:16]2[C:12](=[CH:11][C:10]([N+:7]([O-:9])=[O:8])=[CH:18][CH:17]=2)[CH:13]=[CH:14]1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 4

HCID 679Dimethyl SulfoxideHCID 7498Benzyl BromideHCID 14797Potassium HydroxideHCID 225235-Nitroindole

생성물 1

HCID 98563511-Benzyl-5-nitro-1H-indole수율 51%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
-10 °C

실험 절차

Dry dimethylsulphoxide (20 ml) was added to potassium hydroxide (4.2 g, 0.074 mol) (crushed pellets) and the mixture was stirred under nitrogen for 5 mins. 5-Nitroindole (commerically available) (3.0 g, 0.019 mol) was then added and the red mixture stirred for 30 min at room temperature. The mixture was then cooled to −10° C., benzyl bromide (4.4 ml, 0.037 mol) was slowly added and the mixture stirred and allowed to warm to room temperature over a period of 40 mins. Water (50 ml) was then added and the mixture was extracted with diethyl ether (2×200 ml). The extracts were washed with water (4×50 ml), dried over sodium sulphate and evaporated to leave an oily solid. The excess benzyl bromide was removed by dissolving the whole in diethyl ether (50 ml), diluting this solution with 40-60 petrol (50 ml) and then gradually removing the diethyl ether in vacuo to leave a yellow solid suspended in the petrol. The solid was filtered, washed with copious amounts of 40-60 petrol and dried to give 1-benzyl-5-nitroindole (2.4 g, 51%) as a yellow solid, m.p. 102-104° C.; δH [2H6]-DMSO 8.53 (1H, s, 4-H), 8.00 (1H, d, J 9, 6-H), 7.78 (1H, s, 2-H), 7.68 (1H, d, J 9, 7-H), 7.36-7.20 (5H, m, 2′-H, 3′-H, 4′-H, 5′-H, 6′-H), 6.81 (1H, s, 3-H), 5.52 (2H, s, CH2).

후처리

  1. stirringthe red mixture stirred for 30 min at room temperature
  2. stirringthe mixture stirred
  3. temperatureto warm to room temperature over a period of 40 mins
  4. extractionthe mixture was extracted with diethyl ether (2×200 ml)
  5. washThe extracts were washed with water (4×50 ml)
  6. dry with materialdried over sodium sulphate
  7. customevaporated
  8. customto leave an oily solid
  9. customThe excess benzyl bromide was removed
  10. dissolutionby dissolving the whole in diethyl ether (50 ml)
  11. additiondiluting this solution with 40-60 petrol (50 ml)
  12. customgradually removing the diethyl ether in vacuo
  13. customto leave a yellow solid
  14. filtrationThe solid was filtered
  15. washwashed with copious amounts of 40-60 petrol
  16. customdried

출처 및 근거

ORD 기록
ord-1a2d46101b7b46c89ea0f999f61acc48
출처 데이터셋
uspto-grants-2001_01
특허 번호
US06174889B1

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