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Benzene → p-Fluoro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

HRID 1576844
Notes
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Reaction equation

HRID 1576844 reaction equation
[NH2:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([F:10])=[CH:6][CH:5]=1.C1(C)C(C)=CC=CC=1.N([C:24]1[NH:25][CH2:26][CH2:27][N:28]=1)[N+]([O-])=O.C1C=CC=CC=1>CC(C)=O>[F:10][C:7]1[CH:8]=[CH:9][C:4]([CH:3]([OH:11])[CH2:2][NH:1][C:24]2[NH:28][CH2:27][CH2:26][N:25]=2)=[CH:5][CH:6]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 241BenzeneHCID 7237O-XyleneHCID 98272-Amino-1-(4-fluorophenyl)ethan-1-olHCID 4100422-Nitroamino-2-imidazoline

Product 1

HCID 54097200p-Fluoro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 180
Acetone
Solvent

Conditions

Temperature
160 °C

Procedure

To a solution of 6.5 parts of α-(aminomethyl)-p-fluorobenzyl alcohol in 8 parts of xylene are added 5.2 parts of 2-(nitramino)-2-imidazoline. The mixture is heated in an oil-bath to about 160°C. till gas-evolution is ceased (about 15 minutes). The reaction mixture is cooled and treated with benzene and acetone. The product is sucked off and crystallized from 4-methyl-2-pentanone, yielding p-fluoro-α-(2-imidazolin-2-ylaminomethyl)benzyl alcohol; m.p. 153.4°C.

Workup

  1. custom(about 15 minutes)
  2. temperatureThe reaction mixture is cooled
  3. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-5e07924bcc1c4a1786b6b7b727016d36
Source dataset
uspto-grants-1976_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US03983133

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes