Imidazole → HCID 12773635, compound

HRID 1702767Notes

Reaction equation

HRID 1702767 reaction equation
Cl[C:2]1([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[CH3:20])[C:13]2[CH:12]=[CH:11][S:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1>C(#N)C>[N:21]1([C:2]2([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[CH3:20])[C:13]3[CH:12]=[CH:11][S:10][C:9]=3[C:8]3[C:3]2=[CH:4][CH:5]=[CH:6][CH:7]=3)[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

4

Reactant 2

HCID 795ImidazoleHCID 20525194HCID 20525194, compound

Product 1

HCID 12773635HCID 12773635, compoundYield 62.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

6.1 g (20 mmoles) of crude 4-chloro-4-(2-methyl-phenyl)-4H-indeno[1,2-b]thiophene were taken up in 30 ml of acetonitrile, 4.1 g (60 mmoles) of imidazole were added and the mixture was heated under reflux for 5 hours. The crude product was then precipitated as a syrup by adding 70 ml of water. The supernatant solution was decanted off and the crude product was taken up in ether. The ether solution was dried and evaporated. The residue was taken up in 100 ml of 2 N hydrochloric acid, the insoluble material was separated off and, after cooling, the base was liberated again with sodium hydroxide solution and extracted with ether. The organic phase was dried over sodium sulphate and concentrated. 4.1 g (62.1% of theory) of 4-(imidazol-1-yl)-4-(2-methyl-phenyl)-4H-indeno[1,2-b]thiophene of melting point 75° C. were obtained.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 5 hours
  3. customThe crude product was then precipitated as a syrup
  4. additionby adding 70 ml of water
  5. customThe supernatant solution was decanted off
  6. dry with materialThe ether solution was dried
  7. customevaporated
  8. customthe insoluble material was separated off
  9. temperatureafter cooling
  10. extractionextracted with ether
  11. dry with materialThe organic phase was dried over sodium sulphate
  12. concentrationconcentrated

Sources & evidence

ORD record
ord-98df74daf3184c66bbcb209359001ca7
Source dataset
uspto-grants-1982_09
Patent number
US04349560

Reaction notes

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