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Sodium Cyanide → N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

HRID 1531957
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HRID 1531957 반응식
[C:1](OC)#[N:2].N1C2C(=CC=CC=2)CC1.[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34]Cl)=[C:23]([CH3:33])[C:24]=2[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]1)(=[O:16])[CH3:15].[C-]#N.[Na+]>CC#N.C1OCCOCCOCCOCCOCCOC1>[C:14]([N:17]1[C:25]2[C:20](=[C:21]([CH3:36])[C:22]([CH2:34][C:1]#[N:2])=[C:23]([CH3:33])[C:24]=2[NH:26][C:27](=[O:32])[C:28]([CH3:31])([CH3:30])[CH3:29])[CH2:19][CH2:18]1)(=[O:16])[CH3:15]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 8929Sodium CyanideHCID 10328Indoline2회HCID 137201Cyanic acid, methyl esterHCID 15895572N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

생성물 1

HCID 15524343N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

시약·촉매·용매 2

HCID 28557
18-Crown-6
촉매
HCID 6342Acetonitrile용매

실험 절차

1.27 (9H, S, C(CH3)3), 2.25 (3H, s, -CH3), 2.30 (6H, s, -CH3, >NCOCH3), 3.00 (2H, br, Indoline C3—H), 4.05 (2H, br, Indoline C2—H), 4.68 (2H, s, -CH2c l), 9.16 (1H, br, >NH). (3) N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethyl-propanamide (21 g) was suspended in CH3CN (150 ml), and NaCN (8.1 g) and 18-crown-6 (870 mg) were added, which was followed by refluxing for 15 hr. CH3CN was evaporated under reduced pressure and CHCl3 (300 ml) was added. The mixture was washed with water and dried over anhydrous sodium sulfate. CHCl3 was evaporated under reduced pressure. The obtained residue was washed with boiling MeOH to give 15.5 g of N-(1-acetyl-5-cyanomethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide.

후처리

  1. temperatureby refluxing for 15 hr
  2. customCH3CN was evaporated under reduced pressure and CHCl3 (300 ml)
  3. additionwas added
  4. washThe mixture was washed with water
  5. dry with materialdried over anhydrous sodium sulfate
  6. customCHCl3 was evaporated under reduced pressure
  7. washThe obtained residue was washed with boiling MeOH

출처 및 근거

ORD 기록
ord-56054b5cf45e428ca0a22880c95415e0
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06200988B1

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