2-Nitroamino-2-imidazoline → m-Chloro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

HRID 1576848

Reaction equation

HRID 1576848 reaction equation
[NH2:1][CH2:2][CH:3]([OH:11])[C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([Cl: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>[Cl:10][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][CH:7]=1)[CH:3]([OH:11])[CH2:2][NH:1][C:16]1[NH:20][CH2:19][CH2:18][N:17]=1

Participants

4

Reactant 2

HCID 4100422-Nitroamino-2-imidazolineHCID 37516012-Amino-1-(3-chlorophenyl)ethan-1-ol

Product 1

HCID 54186887m-Chloro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

A mixture of 9.5 parts of α-(aminomethyl)-m-chlorobenzyl alcohol, 7.15 parts of 2-(nitramino)-2-imidazoline and 40 parts of xylene is stirred in an oil-bath at 150°-160°C. while a great part of the xylene is distilled off. The resulting residue is diluted with a few parts of acetone and the product is allowed to crystallize. It is filtered off and crystallized from 4-methyl-2-pentanone, yielding m-chloro-α-(2-imidazolin-2-ylaminomethy)benzyl alcohol; m.p. 108.5°C.

Workup

  1. distillationis distilled off
  2. additionThe resulting residue is diluted with a few parts of acetone
  3. customto crystallize
  4. filtrationIt is filtered off
  5. customcrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-b658a509a6ab4b19972339edb308d00a
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Linked notes

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