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O-Xylene → alpha-(2-Imidazolin-2-ylaminomethyl)-p-methylbenzyl alcohol

HRID 1576850
Notes
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Reaction equation

HRID 1576850 reaction equation
[NH2:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1.N([C:16]1[NH:17][CH2:18][CH2:19][N:20]=1)[N+]([O-])=O.C1(C)C(C)=CC=CC=1>CC(C)=O>[NH:20]1[CH2:19][CH2:18][N:17]=[C:16]1[NH:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][C:7]([CH3:10])=[CH:6][CH:5]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 7237O-XyleneHCID 4100422-Nitroamino-2-imidazolineHCID 35199292-Amino-1-(4-methylphenyl)ethan-1-ol

Product 1

HCID 53928717alpha-(2-Imidazolin-2-ylaminomethyl)-p-methylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
160 °C

Procedure

A mixture of 9.06 parts of α-(aminomethyl)-p-methylbenzyl alcohol, 7.8 parts of 2-(nitramino)-2-imidazoline and 8 parts of xylene is stirred for 30 minutes at 160°C (oil-bath). The reaction mixture is cooled and acetone is added. The precipitated product is filtered off, washed with acetone and dried, yielding α-(2-imidazolin-2-ylaminomethyl)-p-methylbenzyl alcohol; 163.7°C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. filtrationThe precipitated product is filtered off
  3. washwashed with acetone
  4. customdried

Sources & evidence

ORD record
ord-c621f94f9ce7425795b4c019eb926d30
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