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

HRID 1576845

Reaction equation

HRID 1576845 reaction equation
[NH:1]([C:5]1[NH:6][CH2:7][CH2:8][N:9]=1)[N+]([O-])=O.N[CH2:11][CH:12]([OH:20])[C:13]1[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=1>C1(C)C(C)=CC=CC=1>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([CH:12]([OH:20])[CH2:11][NH:1][C:5]2[NH:6][CH2:7][CH2:8][N:9]=2)=[CH:14][CH:15]=1

Participants

4

Reactant 2

HCID 4100422-Nitroamino-2-imidazolineHCID 4124342-Amino-1-(4-chlorophenyl)ethan-1-ol

Product 1

HCID 54043520p-Chloro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent2×

Procedure

To 5.2 parts of 2-(nitramino)-2-imidazoline is added a solution of 7.5 parts of α-(aminomethyl)-p-chlorobenzyl alcohol in 40 parts of xylene while heating. Upon completion, sitrring is continued while heating in an oil-bath at 150°-160°C. and while the xylene is partly distilled off (till gas evolution ceases). The residue is cooled and after the addition of a few parts of acetone, the product is allowed to crystallize. It is filtered off, washed successively with acetone and diisopropylether, dried and the product is recrystallized from 4-methyl-2-pentanone, yielding p-chloro-α-(2-imidazolin-2-ylaminomethyl)benzyl alcohol; m.p. 156°-158°C.

Workup

  1. temperaturewhile heating
  2. distillationis partly distilled off (till gas evolution ceases)
  3. temperatureThe residue is cooled
  4. additionafter the addition of a few parts of acetone
  5. customto crystallize
  6. filtrationIt is filtered off
  7. washwashed successively with acetone and diisopropylether
  8. customdried
  9. customthe product is recrystallized from 4-methyl-2-pentanone

Sources & evidence

ORD record
ord-639571b03b6a485b96f77ebac7b9a34e
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Linked notes

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