Triethylamine → 4-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile

HRID 1919297노트

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HRID 1919297 반응식
[NH2:1][C:2]([CH3:6])([CH3:5])[C:3]#[N:4].C(N(CC)CC)C.[N:14]([C:17]1[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:28])([F:27])[F:26])[CH:18]=1)=[C:15]=[O:16]>ClCCCl>[CH3:5][C:2]1([CH3:6])[C:3](=[NH:4])[N:14]([C:17]2[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[C:19]([C:25]([F:26])([F:27])[F:28])[CH:18]=2)[C:15](=[O:16])[NH:1]1

참가 물질

5

반응물 3

HCID 8471TriethylamineHCID 880222-Amino-2-methylpropionitrileHCID 110637394-Isocyanato-2-(trifluoromethyl)benzonitrile

생성물 1

HCID 221169484-(4,4-Dimethyl-5-imino-2-oxo-1-imidazolidinyl)-2-trifluoromethyl-benzonitrile수율 47.3%

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

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온도
0 °C

실험 절차

To a solution of compound 9 (641 mg, 7.62 mmol) and triethylamine (168 mg, 1.66 mmol) in 1,2 dichloroethane (8.4 mL) at 0° C. under argon was dropwise added a solution of the isocyanate 8a (1.54 g, 7.28 mmol) in 1,2 dichloroethane (3.5 mL). The solution was stirred at 0° C. for 35 min and the ice bath was then removed and stirred at room temperature for an additional 30 min. The solution was then evaporated to dryness and purified by flash chromatography using EtOAc/Hexane (6:4) as an eluant to give pure compound 10a (1.02 g, 47%). 1H NMR (300 MHz, Acetone-d6) δ: 1.54 (m, 6H), 7.45 (broad s, 1H), 8.12 (d, 1H, J=8.46 Hz), 8.29 (dd, 1H, J1=6.90 Hz, J2=1.61 Hz), 8.46 (s, 1H), 8.51 (s, 1H).

후처리

  1. customthe ice bath was then removed
  2. stirringstirred at room temperature for an additional 30 min
  3. customThe solution was then evaporated to dryness
  4. custompurified by flash chromatography

출처 및 근거

ORD 기록
ord-2ea9b9cc3a25451b94dd4117a7368cd1
출처 데이터셋
uspto-grants-2012_05
특허 번호
US08168627B2

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