Malononitrile → HCID 178450345, 화합물

HRID 1297507

반응식

HRID 1297507 반응식
C(O[C:6]1[C:7](=[O:16])[C:8](=[O:15])[C:9]=1[O:10][CH2:11][CH2:12][CH2:13][CH3:14])CCC.[CH2:17]([C:20]#[N:21])[C:18]#[N:19].[CH2:22]([N:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]>C1C=CC=CC=1>[CH2:11]([O:10][C:9]1[C:6](=[C:17]([C:20]#[N:21])[C:18]#[N:19])[C:7](=[O:16])[C:8]=1[O-:15])[CH2:12][CH2:13][CH3:14].[CH2:22]([NH+:24]([CH2:27][CH3:28])[CH2:25][CH3:26])[CH3:23]

참가 물질

5

반응물 3

HCID 8010MalononitrileHCID 8471TriethylamineHCID 65108Dibutyl squarate

생성물 1

HCID 178450345HCID 178450345, 화합물수율 56.4%

시약·촉매·용매 1

HCID 241Benzene용매2회

실험 절차

2.16 ml (10 mmol) of 3,4-dibutoxy-3-cyclobutene-1,2-dione (2b) was dissolved in 20 ml of anhydrous benzene, and 660 mg (10 mmol) of malonodinitrile was added under stirring. Then, 1.65 ml (12 mmol) of triethylamine was added dropwise for 5 min followed by 10 ml of anhydrous benzene. The obtained emulsion is stirred for 30 min at room temperature. The solvent is removed using a rotary evaporator. The yellow oiled residue is treated three times with ether to give crude product 2d (1.8 g, 56%), 1H-NMR (DMSO-d6): δ 10.15–9.55 (1H, broad s, NH+), 4.59 (2H, t, 6.7 Hz, OCH2), 3.07 (6H, q 7.4, 14.5 Hz, N(CH2CH3)3), 1.77–1.58 (2H, m, CH2), 1.48–1.26 (2H, m, CH2), 1.18 (9H, t, 7.3 Hz, N(CH2CH3)3), 0.90 (3H, t, 7.4 Hz, CH3).

후처리

  1. stirringThe obtained emulsion is stirred for 30 min at room temperature
  2. customThe solvent is removed
  3. customa rotary evaporator
  4. additionThe yellow oiled residue is treated three times with ether

출처 및 근거

ORD 기록
ord-e2e5d3fab79d4541a316c228b7dd659f
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07250517B2

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