HCID 12635598, compound → HCID 178526660, compound

HRID 2292835Notes

Reaction equation

HRID 2292835 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.CC(C)([O-])C.[K+]>C(O)(C)(C)C>[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 12635598HCID 12635598, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 178526660HCID 178526660, compound

Reagents, catalysts & solvents 1

HCID 6386tert-ButanolSolvent

Procedure

The thiourea (7) (0.28 g, 0.91 mmole) was suspended in 10 mL of t-butanol and potassium t-butoxide (0.10 g, 0.91 mmole) was then added. The yellow mixture was heated at reflux where the color changed to orange, then slowly back to yellow and accompanied by the precipitation of a solid. Heating was continued for approximately 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 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 0.10 g (40%) of nitroclonidine contaminated by a trace of a higher R1 impurity by TLC.

Workup

  1. temperatureThe yellow mixture was heated
  2. temperatureat reflux where the color
  3. customaccompanied by the precipitation of a solid
  4. temperatureHeating
  5. customthe solvent was then removed on a rotary evaporator
  6. customThe residue was partitioned between 1M HCl and ethyl acetate
  7. filtrationThe resulting yellow solid was collected by filtration
  8. washwashed successively with water and hexane
  9. customair dried
  10. customto provide 0.10 g (40%) of nitroclonidine

Sources & evidence

ORD record
ord-a69aaf75145f417ab51c7c3808101f0a
Source dataset
uspto-grants-1997_11
Patent number
US05684156

Reaction notes

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