Dimethylformamide → 2-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione

HRID 328448

반응식

HRID 328448 반응식
Br[CH:2]1[CH2:6][CH2:5][CH2:4][CH2:3]1.[OH:7][N:8]1[C:12](=[O:13])[C:11]2=[CH:14][CH:15]=[CH:16][CH:17]=[C:10]2[C:9]1=[O:18].C(N(CC)CC)C.CN(C)C=O>O>[CH:2]1([O:7][N:8]2[C:9](=[O:18])[C:10]3=[CH:17][CH:16]=[CH:15][CH:14]=[C:11]3[C:12]2=[O:13])[CH2:6][CH2:5][CH2:4][CH2:3]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8728BromocyclopentaneHCID 10665N-Hydroxyphthalimide

생성물 1

HCID 102632872-(cyclopentyloxy)-1H-isoindole-1,3(2H)-dione수율 49.2%

시약·촉매·용매 1

HCID 962Water용매

실험 절차

A mixture of bromocyclopentane (14.9 g), N-hydroxyphthalimide (16.3 g), triethylamine (15 ml), and dimethylformamide (30 ml) was stirred for 16 hours, then poured into water (500 ml). The oily mixture was extracted with ethyl acetate, and the combined extracts, after washing (water), drying, and removal of solvent gave a white solid. This solid was recrystallised from ethanol to give N-cyclopentyloxyphthalimide (11.37 g, 49%); m.p. 81.2°-82.5°; νmax. (CHBr3) include 1780, 1720 cm-1 (CO-N-CO), 970 cm-1 (>N-O-<CH); τ values (DMSO-d6) 2.08 (4 Ar-H), 5.12 (cyclopentyl 1-H), 8.18 (4-CH2).

후처리

  1. extractionThe oily mixture was extracted with ethyl acetate
  2. washthe combined extracts, after washing (water)
  3. customdrying
  4. customremoval of solvent
  5. customgave a white solid
  6. customThis solid was recrystallised from ethanol

출처 및 근거

ORD 기록
ord-0133c3c6a69c41fd8de38b309e0786c8
출처 데이터셋
uspto-grants-1977_04
특허 번호
US04017515

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