Sodium Hydroxide → HCID 178526722, compound

HRID 744057Notes

Reaction equation

HRID 744057 reaction equation
Cl[C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=1.Br.Br.[NH:13]1[CH:17]=[C:16]([CH2:18][CH2:19][S:20]C(=N)N)[N:15]=[CH:14]1.[OH-].[Na+]>C(O)C.O>[NH:13]1[CH:17]=[C:16]([CH2:18][CH2:19][S:20][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][N:3]=2)[N:15]=[CH:14]1

Participants

6

Reactant 3

HCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridineHCID 178419275HCID 178419275, compound

Product 1

HCID 178526722HCID 178526722, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A hot solution of 0.2 g (1.3 mmol) of 2-chloro-5-nitropyridine in 5 ml of ethanol is added to a solution of 0.2 g (1.1 mmol) of S-{2-[1H-imidazol-4-yl]ethyl}isothiourea dihydrobromide in 2 ml of water. The resulting suspension is stirred under nitrogen. The reaction mixture is cooled to 0°-5° C. and a solution of 4 molar equivalents of sodium hydroxide (0.16 g) in 2 ml of water is added dropwise under N2. The reaction mixture is stirred for 1 h at the same temperature and for 3 h at 21° C. The reaction mixture is evaporated to dryness and the residue is subjected to column chromatography (silica gel) eluted with a gradient mixture of chloroform and methanol (1-10%) to provide the title compound which is then crystallized from 2-propanol, M.p.: 147°-148° C.

Workup

  1. temperatureThe reaction mixture is cooled to 0°-5° C.
  2. stirringThe reaction mixture is stirred for 1 h at the same temperature and for 3 h at 21° C
  3. customThe reaction mixture is evaporated to dryness
  4. washeluted with a gradient mixture of chloroform and methanol (1-10%)

Sources & evidence

ORD record
ord-cae0fd9f26114fc99fc551055446962f
Source dataset
uspto-grants-1996_09
Patent number
US05559113

Reaction notes

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