Hydrochloric Acid → HCID 54537560, compound

HRID 2247898Notes

Reaction equation

HRID 2247898 reaction equation
Cl.[N:2]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11](N)=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=2)[CH:6]=[CH:5][N:4]=[CH:3]1.N([O-])=O.[Na+].[Cu][C:29]#[N:30].[C-]#N.[Na+].C([O-])([O-])=O.[Na+].[Na+].[NH4+].[OH-]>ClC(Cl)Cl.O>[N:2]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:8]2[CH:13]=[CH:12][C:11]([C:29]#[N:30])=[C:10]([N+:15]([O-:17])=[O:16])[CH:9]=2)[CH:6]=[CH:5][N:4]=[CH:3]1

Participants

10

Reactant 7

HCID 313Hydrochloric AcidHCID 8929Sodium CyanideHCID 10340Sodium CarbonateHCID 14923Ammonium HydroxideHCID 23668193Sodium NitriteHCID 53896111HCID 53896111, compoundHCID 178418546HCID 178418546, compound

Product 1

HCID 54537560HCID 54537560, compoundYield 73.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6212ChloroformSolvent2×

Procedure

To 200 ml of cooled (0°-5° C.) HCl 5N were added 19.3 parts of intermediate 51, namely 4-[(1H-imidazol-1-yl)phenylmethyl]-2-nitrobenzenamine, while stirring. When a homogeneous solution was obtained, there was added dropwise a solution of 4.75 parts of sodium nitrite in 40 parts of water at 0°-5° C. Stirring at 0°-5° C. was continued for 1/2 hour and then the mixture was added dropwise to a cooled (0°-5° C.) solution of 5.8 parts of copper(I)cyanide, 6.42 parts of sodium cyanide and 127.1 parts of Na2CO3 (aq.) in a mixture of 700 parts of water and 298 parts of trichloromethane. The whole was left overnight to warm up to room temperature and then there were added NH4OH (aq.) and 447 parts of trichloromethane. After heating at 50° C. for 15 min. and subsequent cooling, the organic layer was separated, dried, filtered and evaporated. The residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH (NH3) 97.5:2.5; CHCl3 /CH3OH 97.5:2.5). The eluent of the desired fractions was evaporated, yielding 14.6 parts (73.2%) of 4-[(1H-imidazol-1-yl)phenylmethyl]-2-nitrobenzonitrile (interm. 52).

Workup

  1. customWhen a homogeneous solution was obtained
  2. stirringStirring at 0°-5° C.
  3. additionthe mixture was added dropwise to
  4. waitThe whole was left overnight
  5. temperatureAfter heating at 50° C. for 15 min.
  6. customsubsequent cooling, the organic layer was separated
  7. customdried
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified twice by column chromatography (silica gel; CHCl3 /CH3OH (NH3) 97.5:2.5; CHCl3 /CH3OH 97.5:2.5)
  11. customThe eluent of the desired fractions was evaporated

Sources & evidence

ORD record
ord-7dcaa6ddebbe43e097fa8eb97836531c
Source dataset
uspto-grants-1991_08
Patent number
US05037829

Reaction notes

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