HomeMCPWorkbenchSkills
HomeWorkbenchNotificationsMe
llms.txt · MCP GuidePrivacy Policy · Terms of Service · Supportv1.8.0
  1. Home
  2. /Reaction

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

HRID 1531957
Notes
Print preview

Reaction equation

HRID 1531957 reaction equation
[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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 8929Sodium CyanideHCID 10328Indoline2×HCID 137201Cyanic acid, methyl esterHCID 15895572N-(1-Acetyl-5-chloromethyl-4,6-dimethylindolin-7-yl)-2,2-dimethylpropanamide

Product 1

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

Reagents, catalysts & solvents 2

HCID 2855718-Crown-6Catalyst
HCID 6342AcetonitrileSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-56054b5cf45e428ca0a22880c95415e0
Source dataset
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06200988B1

Reaction notes

Loading…

On this pageParticipantsProcedureWorkupSources & evidenceReaction notes