O-Xylene → 3,4-Dichloro-alpha-(2-imidazolin-2-ylaminomethyl)benzyl alcohol

HRID 1658255

Reaction equation

[NH2:1][CH2:2][CH:3]([OH:12])[C:4]1[CH:9]=[CH:8][C:7]([Cl:10])=[C:6]([Cl:11])[CH:5]=1.C1(C)C(C)=CC=CC=1.N([C:25]1[NH:26][CH2:27][CH2:28][N:29]=1)[N+]([O-])=O>CC(C)=O>[Cl:11][C:6]1[CH:5]=[C:4]([CH:9]=[CH:8][C:7]=1[Cl:10])[CH:3]([OH:12])[CH2:2][NH:1][C:25]1[NH:29][CH2:28][CH2:27][N:26]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a stirred solution of 8 parts of α(aminomethyl)-3,4-dichlorobenzyl alcohol in 4.5 parts of xylene are added 5.2 parts of 2-(nitramino)-2-imidazoline. The whole is heated in an oil-bath at a temperature of about 160°C. till a clear melt is obtained (about 15 minutes). After cooling to about 60°C., the melt is dissolved in acetone and allowed to crystallize. The precipitated product is filtered off and recrystallized from 20 parts of 4-methyl-2-pentanone, yielding 3,4-dichloro-α-(2-imidazolin 2-ylaminomethyl)benzyl alcohol; m.p. 148°C.

Workup

customis obtained (about 15 minutes)
temperatureAfter cooling to about 60°C.
customto crystallize
filtrationThe precipitated product is filtered off
customrecrystallized from 20 parts of 4-methyl-2-pentanone

Sources & evidence

ORD record: ord-b19a149a41614f8a94dd57c29f724c9f
Source dataset: uspto-grants-1976_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US03963718

Linked notes

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