2-Nitroamino-2-imidazoline → alpha-(2-Imidazolin-2-ylaminomethyl)-m-methylbenzyl alcohol

HRID 1576847

Reaction equation

HRID 1576847 reaction equation
[NH2:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[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>[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][CH:7]=[C:6]([CH3:10])[CH:5]=1

Participants

4

Reactant 2

HCID 4100422-Nitroamino-2-imidazolineHCID 134825112-Amino-1-(3-methylphenyl)ethan-1-ol

Product 1

HCID 53888914alpha-(2-Imidazolin-2-ylaminomethyl)-m-methylbenzyl alcohol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A mixture of 8.2 parts of α-(aminomethyl)-m-methylbenzyl alcohol, 6,1 parts of 2-(nitramino)-2-imidazoline and 40 parts of xylene is stirred in an oil-bath at 150°-160°C, while almost all xylene is distilled off. The residue is diluted with a few parts of acetone and allowed to crystallize. The product is filtered off and recrystallized from 4-methyl-2-pentanone, yielding α-(2-imidazolin-2-ylaminomethyl)-m-methylbenzyl alcohol; m.p. 121°C.

Workup

  1. distillationwhile almost all xylene is distilled off
  2. additionThe residue is diluted with a few parts of acetone
  3. customto crystallize
  4. filtrationThe product is filtered off
  5. customrecrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-522e6db6ff9344f395e2cbef978ae442
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Linked notes

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