N-3-Bromopropylphthalimide → HCID 20186606, 화합물

HRID 464342

반응식

HRID 464342 반응식
[H-].[Na+].[C:3]1([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[H][H].Br[CH2:19][CH2:20][CH2:21][N:22]1[C:26](=[O:27])[C:25]2=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]2[C:23]1=[O:32]>CS(C)=O.CCOCC.O>[C:3]1([N:9]([CH2:19][CH2:20][CH2:21][N:22]2[C:26](=[O:27])[C:25]3=[CH:28][CH:29]=[CH:30][CH:31]=[C:24]3[C:23]2=[O:32])[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][N:11]=2)[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

참가 물질

8

반응물 4

HCID 21611N-3-BromopropylphthalimideHCID 24758Sodium hydrideHCID 81130N-2-PyridylanilineHCID 178418361HCID 178418361, 화합물

생성물 1

HCID 20186606HCID 20186606, 화합물수율 35.1%

시약·촉매·용매 3

HCID 679Dimethyl Sulfoxide용매3회HCID 962Water용매HCID 3283Diethyl Ether용매

반응 조건

온도
85 °C

실험 절차

To a suspension of sodium hydride (0.78 g) in DMSO (20 ml) was added 2-(N-phenylamino)pyridine (5.0 g) in DMSO (15 ml). The mixture was stirred and slowly heated under nitrogen to 85° C. After the evolution of hydrogen had ceased the mixture was cooled to room temperature and N-(3-bromopropyl)phthalimide (7.88 g) in DMSO (15 ml) added dropwise. After standing overnight the mixture was poured into water and ether extracts made with the pH adjusted between 2 to 4. The extracts were dried (MgSO4), stripped and the residue crystallised from ethanol to give N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide, 3.69 g (35%) mp 103°-5° C. (ii) N-[3-(N-phenyl-N-pyrid-2-ylamino)propyl]phthalimide (3.1 g) and conc. hydrochloric acid (30 ml) were heated under reflux for 21 hr. Phthalic acid was filtered off on cooling and the filtrate stripped. The residue was taken back up in water and the solution extracted at pH 1 with chloroform. The pH was raised to 13 (NaOH) and the solution extracted again with ether. The ether extracts were dried (K2CO3) and stripped to give 2-[N-(3-aminopropyl)-N-phenylamino]pyridine, 1.84 g as an oil. (iii) 2-[N-(3-aminopropyl)-N-phenylamino]pyridine (0.9 g) and 2-nitroamino-5-(6-methylpyrid-3-ylmethyl)pyrimid-4-one (0.86 g) were heated together under reflux in pyridine (2.5 ml) for 24 hr. The mixture was stripped and the residue recrystallised from ethanol to give 2-[3-(N-phenyl-N-pyrid-2-ylamino) propylamino]-5-(6-methylpyrid-3-ylmethyl) pyrimid-4-one, 1.03 g (73%) mp 216°-18° C.

후처리

  1. temperaturewas cooled to room temperature
  2. dry with materialThe extracts were dried (MgSO4)
  3. customthe residue crystallised from ethanol

출처 및 근거

ORD 기록
ord-8f12a38712d14c30b972ba9717c69390
출처 데이터셋
uspto-grants-1985_10
특허 번호
US04547506

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