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

HRID 5290

反応式

HRID 5290 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a06527d7605c46b0b8ec403e13acd486
出典データセット
uspto-grants-1993_09
特許番号
US05244763

関連ノート

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