Sodium Hydroxide → HCID 178526719, compound

HRID 726248Notes

Reaction equation

HRID 726248 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][NH:6][CH:7]=1.[NH2:8][C:9](N)=[S:10].ClC1[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15]N=1.[OH-].[Na+]>C(O)C.O>[NH:6]1[CH:7]=[C:3]([CH2:2][S:10][C:9]2[CH:18]=[CH:17][C:16]([N+:19]([O-:21])=[O:20])=[CH:15][N:8]=2)[N:4]=[CH:5]1

Participants

7

Reactant 4

HCID 14798Sodium HydroxideHCID 783082-Chloro-5-nitropyridineHCID 2723790ThioureaHCID 178478442HCID 178478442, compound

Product 1

HCID 178526719HCID 178526719, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolvent3×HCID 962WaterSolvent2×

Conditions

Temperature
21 °C

Procedure

A mixture of 0.6 g (3.9 mmol) of 4-chloromethylimidazole and of an equimolar equivalent of thiourea (0.3 g) in 10 ml of ethanol is brought to reflux for 30 min. 5 ml of ethanol, 20 ml of water and 1.2 molar equivalents of 2-chloro-5-nitropyridine (0.74 g) in 5 ml of hot ethanol are added to this mixture. The light solution is cooled to 0°-10° C. in an ice bath and a solution of 0.49 g of sodium hydroxide in 10 ml of water is added dropwise under nitrogen at 0°-10° C. and then the mixture is stirred for a further 3 h at 21° C. The precipitate is collected, washed with water and chromatographed through silica gel with a mixture of chloroform and methanol (1°-20%) to give the title compound, M.p.: 155°-156° C.

Workup

  1. temperatureto reflux for 30 min
  2. temperatureThe light solution is cooled to 0°-10° C. in an ice bath
  3. customThe precipitate is collected
  4. washwashed with water
  5. customchromatographed through silica gel with a mixture of chloroform and methanol (1°-20%)

Sources & evidence

ORD record
ord-3699e0d70f9148778946c69af0aca102
Source dataset
uspto-grants-1998_01
Patent number
US05708171

Reaction notes

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