Benzylamine → HCID 178526660, compound

HRID 2292837Notes

Reaction equation

HRID 2292837 reaction equation
[NH2:1][CH2:2][CH2:3][NH:4][C:5]([NH:7][C:8]1[C:13]([Cl:14])=[CH:12][C:11]([N+:15]([O-:17])=[O:16])=[CH:10][C:9]=1[Cl:18])=S.C(N)C1C=CC=CC=1>C1(C)C=CC=CC=1>[Cl:18][C:9]1[CH:10]=[C:11]([N+:15]([O-:17])=[O:16])[CH:12]=[C:13]([Cl:14])[C:8]=1[N:7]=[C:5]1[NH:4][CH2:3][CH2:2][NH:1]1

Participants

4

Reactant 2

HCID 7504BenzylamineHCID 12635598HCID 12635598, compound

Product 1

HCID 178526660HCID 178526660, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The thiourea (7) (0.36 g, 1.1 mmole) was suspended in 10 mL of toluene and excess benzylamine (1 mL) was then added. The mixture was heated at reflux for approximately 4 hours, and the solvent was then removed on a rotary evaporator. The residue was partitioned between 1M HCl and ethyl acetate. The aqueous phase was brought to pH 8-9 with 1N NaOH. The resulting yellow solid was collected by filtration, washed successively with water and hexane, and then air dried to provide 0.05 g (15%) of nitroclonidine.

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for approximately 4 hours
  3. customthe solvent was then removed on a rotary evaporator
  4. customThe residue was partitioned between 1M HCl and ethyl acetate
  5. filtrationThe resulting yellow solid was collected by filtration
  6. washwashed successively with water and hexane
  7. customair dried
  8. customto provide 0.05 g (15%) of nitroclonidine

Sources & evidence

ORD record
ord-ae5a8d14d40d4395bb67548e2d6866be
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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