1-Bromo-3,6-dioxaheptane → 3-(2-(2-Methoxyethoxy)ethylamino)-5-amino-4-chlorobenzonitrile

HRID 921865노트

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HRID 921865 반응식
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH2:11])[C:9]=1[Cl:10])[C:5]#[N:6].Br[CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19]>CN(C=O)C.CCOC(C)=O.O>[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([NH:11][CH2:13][CH2:14][O:15][CH2:16][CH2:17][O:18][CH3:19])[C:9]=1[Cl:10])[C:5]#[N:6]

참가 물질

6

반응물 2

HCID 1235321-Bromo-3,6-dioxaheptaneHCID 124029953,5-Diamino-4-chlorobenzonitrile

생성물 1

HCID 899226323-(2-(2-Methoxyethoxy)ethylamino)-5-amino-4-chlorobenzonitrile수율 28.2%

시약·촉매·용매 3

HCID 962Water용매HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

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온도
100 °C

실험 절차

To a solution of 3,5-diamino-4-chlorobenzonitrile (220 mg, 1.313 mmol) in DMF (3 mL) was added IIlunig's Base (2.75 mL, 15.75 mmol) followed by 1-bromo-2-(2-methoxyethoxy)ethane (1442 mg, 7.88 mmol). The resulting solution was heated at 100° C. for 16 h. LC-MS indicated ca. 30% conversion. It was diluted with EtOAc and water. After separating the layers, the aqueous layer was further extracted with EtOAc. The combined organic extracts were washed with water, brine, dried over MgSO4, filtered and concentrated. Purification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g) gave 3-amino-4-chloro-5-((2-(2-methoxyethoxy)ethyl)amino)benzonitrile (100 mg) as an orange oil.

후처리

  1. customAfter separating the layers
  2. extractionthe aqueous layer was further extracted with EtOAc
  3. washThe combined organic extracts were washed with water, brine
  4. dry with materialdried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customPurification via silica gel chromatography (0-70% EtOAc in Hexanes, 24 g)

출처 및 근거

ORD 기록
ord-bdc587d5c255475392306778bfcbba6d
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09273057B2

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