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

HRID 231281ノート

反応式

HRID 231281 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 241Benzene溶媒HCID 6212Chloroform溶媒

実験手順

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.

後処理

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

出典と根拠

ORDレコード
ord-65f181d65017461e9db482bd41ec9c6f
出典データセット
uspto-grants-1989_07
特許番号
US04845233

反応ノート

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