Isopropylamine → HCID 86662609, 화합물

HRID 1404724노트

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HRID 1404724 반응식
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]

참가 물질

6

반응물 4

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

생성물 1

HCID 86662609HCID 86662609, 화합물

시약·촉매·용매 1

HCID 3283Diethyl Ether용매2회

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온도
10 °C

실험 절차

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%): by 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); EIMS m/z 187.

후처리

  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
  7. customby 145° C.

출처 및 근거

ORD 기록
ord-1c18208b4c074cd39334e6d796ef38b7
출처 데이터셋
uspto-grants-2014_12
특허 번호
US08912338B2

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