Cyanogen Bromide → 1-[(4-Chlorophenyl)methyl]-4,5-dihydro-1H-imidazol-2-amine hydrochloride

HRID 236011Notes

Reaction equation

HRID 236011 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][NH:9][CH2:10][CH2:11][NH2:12])=[CH:4][CH:3]=1.[N:13]#[C:14]Br>CO>[ClH:1].[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][N:9]2[CH2:10][CH2:11][N:12]=[C:14]2[NH2:13])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 10476Cyanogen BromideHCID 13785698N-(4-chlorobenzyl)ethane-1,2-diamine

Product 1

HCID 202177121-[(4-Chlorophenyl)methyl]-4,5-dihydro-1H-imidazol-2-amine hydrochloride

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

The amine produced in Procedure 90, 14.5 g. (0.079 mole) was dissolved in 50 ml. of methanol and treated with a solution 9.1 g. (0.086 mole) of cyanogen bromide in 30 ml. of methanol in dropwise fashion. The warm solution was cooled to room temperature which resulted in the formation of a precipitate. The mixture was kept with stirring for 1/2 hr. and then a portion of the solvent was removed by distillation in vacuo. The solid product which separated was collected on a filter, washed with Et2O, and air dried, yield 16 g., m.p. 270°-272°.

Workup

  1. dissolution(0.079 mole) was dissolved in 50 ml
  2. customresulted in the formation of a precipitate
  3. customand then a portion of the solvent was removed by distillation in vacuo
  4. customThe solid product which separated
  5. customwas collected on a filter
  6. washwashed with Et2O, and air
  7. customdried

Sources & evidence

ORD record
ord-88588e1ea8604fde9481a7ede944d609
Source dataset
uspto-grants-1987_02
Patent number
US04642345

Reaction notes

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