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

Toluene → N,N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine

HRID 3023
Notes
Print preview

Reaction equation

HRID 3023 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=1.I[C:11]1[CH:12]=[C:13]([CH:21]=[CH:22][CH:23]=1)[CH2:14][CH2:15][C:16]([O:18][CH2:19][CH3:20])=[O:17].[C:24](=[O:27])([O-])[O-:25].[K+].[K+].CCCCC[CH2:35][CH2:36][CH2:37][CH2:38][CH2:39][CH2:40][CH2:41][CH3:42].[C:43]1(C)C=CC=C[CH:44]=1>O.O.O.O.O.S([O-])([O-])(=O)=O.[Cu+2]>[CH2:19]([O:18][C:16]([CH2:15][CH2:14][C:13]1[CH:12]=[C:11]([N:1]([C:41]2[CH:40]=[CH:39][CH:38]=[C:37]([CH2:36][CH2:35][C:24]([O:25][CH2:43][CH3:44])=[O:27])[CH:42]=2)[C:2]2[CH:7]=[CH:6][C:5]([CH3:8])=[C:4]([CH3:9])[CH:3]=2)[CH:23]=[CH:22][CH:21]=1)=[O:17])[CH3:20]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 5

HCID 1140TolueneHCID 72483,4-DimethylanilineHCID 11430Potassium CarbonateHCID 12388TridecaneHCID 10913723Ethyl 3-iododihydrocinnamate

Product 1

HCID 18931917N,N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine

Reagents, catalysts & solvents

1
HCID 24463Copper sulfate pentahydrateCatalyst

Conditions

Temperature
230 °C

Procedure

In a 100 ml-volume flask, 6 g of 3,4-xylidine, 34 g of ethyl 3-iododihydrocinnamate, 19 g of potassium carbonate, 5 g of copper sulfate pentahydrate and 20 ml of n-tridecane were placed, and the mixture was reacted under heating at 230° C. for 10 hours in a nitrogen stream. After the reaction, the system was cooled to room temperature, the reaction mixture was dissolved in 50 ml of toluene, insoluble matters were filtered, and the filtrate was purified by silica gel column chromatography using toluene to obtain 20 g of N, N-bis[3-(2-ethoxycarbonylethyl)phenyl]-3,4-xylidine as an oily substance. The IR spectrum of the product is shown in FIG. 1.

Workup

  1. customthe mixture was reacted
  2. customAfter the reaction
  3. temperaturethe system was cooled to room temperature
  4. filtrationinsoluble matters were filtered
  5. customthe filtrate was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-065831d99277499b89b8f6f92e86ad30
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731118

Reaction notes

Loading…

On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes