N-bromobutanimide → HCID 68615032, compound

HRID 1776072Notes

Reaction equation

HRID 1776072 reaction equation
[CH3:1][C:2]1[CH:21]=[CH:20][CH:19]=[CH:18][C:3]=1[N:4]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[CH3:11].C1C(=O)N([Br:29])C(=O)C1.ClCCl.[Cl-].[Na+].O>ClCCl>[Br:29][C:15]1[CH:14]=[CH:13][C:12]([N:4]([C:3]2[CH:18]=[CH:19][CH:20]=[CH:21][C:2]=2[CH3:1])[C:5]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[CH3:11])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 67184N-bromobutanimideHCID 227213082-Methyl-N-(2-methylphenyl)-N-phenylaniline2×HCID 131726697Dichloromethane brine

Product 1

HCID 68615032HCID 68615032, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 2-methyl-N-phenyl-N-(o-tolyl)aniline (Compound 10) (8.2 g, 30 mmol) in dichloromethane (DCM) (100 mL), was added n-bromosuccinimide (NBS) (5.34 g, 30 mmol) at about 0° C. and stirred for about 4 hours. The resulting mixture was worked up with dichloromethane/brine, dried over Na2SO4, loaded on silica gel and purified by flash column using eluents of hexanes to hexanes/dichloromethane 9:1. The desired fraction was collected, and removal of solvent gave a white solid (Compound 11) (10.7 g, in 100% yield).

Workup

  1. dry with materialdried over Na2SO4
  2. custompurified by flash column
  3. customThe desired fraction was collected
  4. customremoval of solvent

Sources & evidence

ORD record
ord-1827ef4a60ba4cb3adb0f5b7c2953004
Source dataset
uspto-grants-2016_02
Patent number
US09263681B2

Reaction notes

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