Hydrochloric Acid → 2-(3,4,5-Triacetoxybenzamido)ethyl methacrylate

HRID 5290

반응식

HRID 5290 반응식
[C:1]([O:4][C:5]1[CH:6]=[C:7]([CH:11]=[C:12]([O:18][C:19](=[O:21])[CH3:20])[C:13]=1[O:14][C:15](=[O:17])[CH3:16])[C:8](Cl)=[O:9])(=[O:3])[CH3:2].Cl.[C:23]([O:28][CH2:29][CH2:30][NH2:31])(=[O:27])[C:24]([CH3:26])=[CH2:25].C(N(CC)CC)C.Cl>C(Cl)Cl>[C:23]([O:28][CH2:29][CH2:30][NH:31][C:8](=[O:9])[C:7]1[CH:6]=[C:5]([O:4][C:1](=[O:3])[CH3:2])[C:13]([O:14][C:15](=[O:17])[CH3:16])=[C:12]([O:18][C:19](=[O:21])[CH3:20])[CH:11]=1)(=[O:27])[C:24]([CH3:26])=[CH2:25]

참가 물질

6

반응물 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 75495Aminoethyl methacrylate hydrochlorideHCID 1555063,4,5-Triacetoxybenzoyl chloride

생성물 1

HCID 197954682-(3,4,5-Triacetoxybenzamido)ethyl methacrylate

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

3,4,5-Triacetoxybenzoyl chloride (0.050 mol) was dissolved in 100 mL CH2Cl2 at 0° C. To this was added 2-aminoethyl methacrylate hydrochloride (8.28 g, 0.050 mol), followed by dropwise addition of triethylamine (14.63 mL, 0.105 mol). After 30 min, 100 mL 1N HCl was added with vigorous stirring. The organic layer was isolated, washed with saturated NaHCO3 and 50 mL 1N HCl, dried over MgSO4, and evaporated to give an oil, which crystallized rapidly after the addition of 50 mL diethyl ether. The product was isolated by filtration and vacuum dried. Yield, 17.97 g as a white solid, 88%. 1H NMR (300 MHz, CDCl3), δ1.92 (s, 3H), 2.26 (s, 6H), 2.27 (s, 3H), 3.68 (m, 2H), 4.30 (t, 2H), 5.58 (m, 1H), 6.11 (s, 1H), 6.66 (t, broad, 1H), 7.51 (s, 2H). Anal., calcd for C19H21N1O9C 56.02, H 5.20, N 3.44, found C 55.99, H 5.15, N 3.50.

후처리

  1. customThe organic layer was isolated
  2. washwashed with saturated NaHCO3 and 50 mL 1N HCl
  3. dry with materialdried over MgSO4
  4. customevaporated
  5. customto give an oil, which
  6. customcrystallized rapidly
  7. additionafter the addition of 50 mL diethyl ether
  8. customThe product was isolated by filtration and vacuum
  9. customdried
  10. customYield

출처 및 근거

ORD 기록
ord-a06527d7605c46b0b8ec403e13acd486
출처 데이터셋
uspto-grants-1993_09
특허 번호
US05244763

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