Hydrochloric Acid → HCID 178526660, compound

HRID 2292836Notes

Reaction equation

HRID 2292836 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.N1C=CN=C1.Cl>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

5

Reactant 3

HCID 313Hydrochloric AcidHCID 795ImidazoleHCID 12635598HCID 12635598, compound

Product 1

HCID 178526660HCID 178526660, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The thiourea (7) (0.50 g, 1.6 mmole) was suspended in 10 mL of toluene and imidazole (0.16 g, 1.6 mmole) was then added. The yellow mixture was heated at reflux for approximately 24 hours, then cooled to ambient temperature and treated with 1M HCl. The aqueous phase was separated, the toluene phase was extracted with 1M HCl, and the combined aqueous phases were 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 0.30 g (68%) of nitroclonidine contaminated by a trace of a higher Rf impurity by TLC.

Workup

  1. temperatureThe yellow mixture was heated
  2. temperatureat reflux for approximately 24 hours
  3. customThe aqueous phase was separated
  4. extractionthe toluene phase was extracted with 1M HCl
  5. filtrationThe resulting yellow solid was collected by filtration
  6. washwashed successively with water and hexane
  7. customair dried
  8. customto provide 0.30 g (68%) of nitroclonidine

Sources & evidence

ORD record
ord-d90237457e114a42b478175c790f4c68
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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