Chloroacetyl chloride → 2-Chloro-N-(phenanthridin-6-ylmethyl)acetamide

HRID 718741

반응식

HRID 718741 반응식
C(N(CC)CC)C.[Cl:8][CH2:9][C:10](Cl)=[O:11].[CH:13]1[C:26]2[C:17](=[N:18][C:19]([CH2:27][NH2:28])=[C:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)[CH:16]=[CH:15][CH:14]=1>C(Cl)Cl>[Cl:8][CH2:9][C:10]([NH:28][CH2:27][C:19]1[N:18]=[C:17]2[C:26](=[C:25]3[C:20]=1[CH:21]=[CH:22][CH:23]=[CH:24]3)[CH:13]=[CH:14][CH:15]=[CH:16]2)=[O:11]

참가 물질

5

반응물 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 11506715HCID 11506715, 화합물

생성물 1

HCID 867124842-Chloro-N-(phenanthridin-6-ylmethyl)acetamide

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

실험 절차

Triethylamine (460 μL, 3.30 mmol), followed by a solution of chloroacetyl chloride (175 μL, 2.20 mmol) in CH2Cl2 (5 mL) were added dropwise over 5 minutes to a solution of the amine 8 (229 mg, 1.10 mmol) dissolved in CH2Cl2 (15 mL) at 0° C. The reaction mixture was then allowed to warm to ambient temperature and stirred for 2 hours. The solvent was removed under reduced pressure and the reaction crude purified via flash chromatography over silica eluting with a gradient of CH2Cl2 to 1% MeOH/99% CH2Cl2. Evaporation of the solvents under reduced pressure yielded the chloro 9 as an off-white solid (177 mg, 56.5% over three steps).

후처리

  1. customThe solvent was removed under reduced pressure
  2. customthe reaction crude
  3. custompurified via flash chromatography over silica eluting with a gradient of CH2Cl2 to 1% MeOH/99% CH2Cl2
  4. customEvaporation of the solvents under reduced pressure

출처 및 근거

ORD 기록
ord-8dcc7611d281468ebbcd8120706b5eef
출처 데이터셋
uspto-grants-2015_11
특허 번호
US09194802B2

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