Sodium hydride → 1-Ethyl-4-imidazolin-2-one 3-alpha-ethyltetradecanoate

HRID 231281노트

반응식

HRID 231281 반응식
[CH2:1]([N:3]1[CH:7]=[CH:6][NH:5][C:4]1=[O:8])[CH3:2].ClC([O:12][C:13](=[O:27])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])C.[H-].[Na+]>C(Cl)(Cl)Cl.C1C=CC=CC=1>[CH2:1]([N:3]1[CH:7]=[CH:6][NH:5][C:4]1=[O:8])[CH3:2].[CH2:1]([CH:15]([CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH3:26])[CH2:14][C:13]([O-:12])=[O:27])[CH3:2]

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 140652901-ethyl-1,3-dihydro-2H-imidazol-2-oneHCID 142456981-Chloroethyltetradecanoate

생성물 1

HCID 867432111-Ethyl-4-imidazolin-2-one 3-alpha-ethyltetradecanoate수율 10%

시약·촉매·용매 2

HCID 241Benzene용매HCID 6212Chloroform용매

실험 절차

1-Ethyl-4-imidazolin-2-one (1 gm, 0.009 mol) and 1-chloroethyltetradecanoate (2.6 gm, 0.009 mol) were dissolved in 13 ml of dry chloroform and a suspension of sodium hydride in dry benzene (3 ml) was added portionwise. The reaction mixture was stirred at room temperature overnight and was followed by the workup presented in the preceeding examples. After purification by liquid chromatography using silica gel as the supporting material and chloroform as the eluant (EM Silica gel 500 G, 60-200 mesh was used), 1-ethyl-4-imidazolin-2-one-3-α-ethyltetradecanoate was obtained in a yield of 10% (350 mg). 1H n.m.r.(CC14): δ0.90(3H, t, J=5 Hz, CH3 [CH2 ]11CH2 --); 1.28(22H, s, broad, CH3 [CH2 ]11CH2 --); 1.30(3H, t, J=7 Hz, CH3CH2N--); 1.61(3H, d, J=6 Hz, --CHCH3 --); 2.25(2H, t, J=6 Hz, CH3 [CH2 ]10CH2 --); 3.60(2H, q, J=6 Hz, CH3CH2N--); 6.10(1H, d, J=3 Hz, HC=CH); 6.23(1H, d, J=3 Hz, HC=CH); 6.43(1H, q, J=6 Hz, CH3CH--). νmax (film): 3200, 3180(HC=CH), 1745, 1705, 1690(C=O); 1250 cm-1 (C-O-C). m/e+1 367, C21H38N2O3 requires 366.

후처리

  1. additionwas added portionwise
  2. customAfter purification by liquid chromatography

출처 및 근거

ORD 기록
ord-65f181d65017461e9db482bd41ec9c6f
출처 데이터셋
uspto-grants-1989_07
특허 번호
US04845233

반응 노트

불러오는 중…