Cesium carbonate → HCID 178526660, compound

HRID 2292834Notes

Reaction equation

HRID 2292834 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(=O)([O-])[O-].[Cs+].[Cs+]>C(O)CC>[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 10796Cesium carbonateHCID 12635598HCID 12635598, compound

Product 1

HCID 178526660HCID 178526660, compound

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent

Procedure

The thiourea (7) (0.50 g, 1.6 mmole) was suspended in 10 mL of n-propanol and cesium carbonate (0.53 g, 1.6 mmole) was added. The yellow suspension was stirred at ambient temperature for approximately 30 minutes, when the color changed from yellow to orange. The mixture was heated at reflux for about 24 hours, and the solvent was then removed on a rotary evaporator. The residue was partitioned between 1M HCl and ethyl acetate and the aqueous phase was brought to a pH of 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 0.10 g (23%) of nitroclonidine (3).

Workup

  1. temperatureThe mixture was heated
  2. temperatureat reflux for about 24 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

Sources & evidence

ORD record
ord-2015557e2ba04f078a7b7b04d0a9dd3b
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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