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Water → (4-Bromobenzylidene)(1-isopropyl-2-methylpropyl)amine

HRID 260536
Notes
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Reaction equation

HRID 260536 reaction equation
[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=O)=[CH:4][CH:3]=1.[CH3:10][CH:11]([CH:13]([NH2:17])[CH:14]([CH3:16])[CH3:15])[CH3:12].O>C1(C)C=CC=CC=1.C1(C)C=CC(S(O)(=O)=O)=CC=1>[Br:1][C:2]1[CH:9]=[CH:8][C:5]([CH:6]=[N:17][CH:13]([CH:14]([CH3:16])[CH3:15])[CH:11]([CH3:12])[CH3:10])=[CH:4][CH:3]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 962WaterHCID 707414-BromobenzaldehydeHCID 777023-Pentanamine, 2,4-dimethyl-

Product 1

HCID 15225580(4-Bromobenzylidene)(1-isopropyl-2-methylpropyl)amineYield 94.9%

Reagents, catalysts & solvents 2

HCID 6101p-Toluenesulfonic acidCatalyst
HCID 1140
Toluene
Solvent

Procedure

A mixture of 4-bromobenzaldehyde (7.3 g, 40.0 mmol), 2,4-dimethylpent-3-ylamine (4.8 g, 41.4 mmol), and para-toluenesulfonic acid (0.05 g, 0.29 mmol) in 125 mL of toluene was heated under reflux while water was removed with a Dean-Stark trap. The toluene then was removed under vacuum and distillation of the remaining residue gave (4-bromobenzylidene)(1-isopropyl-2-methylpropyl)amine (10.71 g) as a clear colorless oil.

Workup

  1. temperaturewas heated
  2. customwas removed with a Dean-Stark trap
  3. customThe toluene then was removed under vacuum and distillation of the remaining residue

Sources & evidence

ORD record
ord-11674302c7c4417794db355ac1ddbba3
Source dataset
uspto-grants-1996_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05527918

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes