Isopropylamine → HCID 86662609、化合物

HRID 1911982ノート

反応式

HRID 1911982 の反応式
C([Li])CCC.C(N)(C)C.[C:10]([CH:12]([CH3:18])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11].Cl[CH2:20][S:21][CH2:22]Cl>CCOCC>[C:10]([C:12]([CH3:18])([CH2:20][S:21][CH3:22])[C:13]([O:15][CH2:16][CH3:17])=[O:14])#[N:11]

参加物

6

反応物 4

HCID 6363IsopropylamineHCID 98018Ethyl 2-cyanopropionateHCID 565560Bis(chloromethyl) sulfideHCID 178418339Butyllithium

生成物 1

HCID 86662609HCID 86662609、化合物

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒2 回

反応条件

温度
10 °C

実験手順

n-Butyllithium (24.2 mL, 60 mmol, 2.5 M solution in hexanes) was added to a solution of iso-propylamine (8.1 mL, 58 mmol) in dry ether (70 mL) under nitrogen at a rate needed to maintain temperature below −60° C. Upon completion, the reaction was allowed to warm to 10° C., re-cooled to −78° C. before addition of ethyl 2-cyanopropanoate (7 g, 55 mmol). After stirring at −78° C. for 90 minutes, chloromethylsulfide (4.61 mL, 55 mmol) was added and the mixture was warmed to room temperature over 14 hours, diluted with ether (350 mL), washed with water (100 mL), brine (100 mL), dried over MgSO4, concentrated under reduced pressure and distilled at 0.04 mm Hg. Yield of yellow liquid 3.95 g. (38%): bp 145° C.; IR (KBr thin film) 1751 cm−1; 1H NMR (400 MHz, CDCl3) δ 4.30 (q, J=7.1 Hz, 2H), 3.08 (d, J=13.9 Hz, 1H), 2.91 (d, J=13.9 Hz, 1H), 2.30 (s, 3H), 1.67 (s, 3H), 1.35 (t, J=7.4 Hz, 3H); ESIMS m/z 187.

後処理

  1. temperatureto maintain temperature below −60° C
  2. temperaturethe mixture was warmed to room temperature over 14 hours
  3. washwashed with water (100 mL), brine (100 mL)
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. distillationdistilled at 0.04 mm Hg

出典と根拠

ORDレコード
ord-4c3debcac00742a2aa46ffd7d356236b
出典データセット
uspto-grants-2013_12
特許番号
US08604211B2

反応ノート

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