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

HRID 258647

反応式

HRID 258647 の反応式
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

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 8728BromocyclopentaneHCID 10665N-Hydroxyphthalimide

生成物 1

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

試薬・触媒・溶媒 1

HCID 962Water溶媒

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-2f32ca15da8549069242d04abc088488
出典データセット
uspto-grants-1977_07
特許番号
US04033950

関連ノート

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