Triethylamine → N-(Acryloyloxyethoxyethyl)hexahydrophthalimide

HRID 259662

반응식

HRID 259662 반응식
[OH:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:9]2[C:8]1=[O:17].C(N(CC)CC)C.[C:25](Cl)(=[O:28])[CH:26]=[CH2:27]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1.CC(C)=O>[C:25]([O:1][CH2:2][CH2:3][O:4][CH2:5][CH2:6][N:7]1[C:11](=[O:12])[CH:10]2[CH2:13][CH2:14][CH2:15][CH2:16][CH:9]2[C:8]1=[O:17])(=[O:28])[CH:26]=[CH2:27]

참가 물질

6

반응물 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 55023972N-(2-hydroxyethoxyethyl)hexahydrophthalimide

생성물 1

HCID 67622109N-(Acryloyloxyethoxyethyl)hexahydrophthalimide수율 59.5%

시약·촉매·용매 2

HCID 7108Phenothiazine촉매HCID 180Acetone용매

실험 절차

A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 100 g of N-(2-hydroxyethoxyethyl)hexahydrophthalimide (0.41 mol.), 42 g of triethylamine (0.41 mol.), 1 g of phenothiazine and 400 ml of acetone. Next, 38 g of acryloyl chloride (0.41 mol.) was added slowly to the flask via the addition funnel over 45 minutes. The reaction was stirred for an additional 12 hours. The triethylamine hydrochloride salt was removed by filtration and the remaining mother liquor was evaporated with a rotoevaporator. The resulting red-orange liquid was dissolved in chloroform and extracted with HCl(10%), NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 72 g (59%) of an orange-red liquid. The product was confirmed by IR and 13C NMR.

후처리

  1. customA one liter, three necked flask was equipped with overhead stirrer
  2. customThe triethylamine hydrochloride salt was removed by filtration
  3. customthe remaining mother liquor was evaporated with a rotoevaporator
  4. dissolutionThe resulting red-orange liquid was dissolved in chloroform
  5. extractionextracted with HCl(10%), NaCl(aq.), NH4OH(10%), NaCl(aq.)
  6. dry with materialdried over MgSO4
  7. customThe chloroform was removed with a rotoevaporator

출처 및 근거

ORD 기록
ord-e4ba0c99ac55476c974c9b8056f79017
출처 데이터셋
uspto-grants-1996_06
특허 번호
US05523152

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