HCID 70593817, compound → HCID 70598459, compound

HRID 2057376Notes

Reaction equation

HRID 2057376 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:13]2=[N:14][CH2:15][CH2:16][N:12]2[CH:11](O)[CH2:10]1>Cl>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([CH3:8])[C:3]=1[N:9]1[C:13]2=[N:14][CH2:15][CH2:16][N:12]2[CH:11]=[CH:10]1

Participants

3

Reactant 1

HCID 70593817HCID 70593817, compound

Product 1

HCID 70598459HCID 70598459, compoundYield 23.9%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

5 gm (0.02 mol) of 7-(2-chloro-6-methyl-phenyl)-5-hydroxy-2,3,5,6-tetrahydro-imidazo[1,2-α]-imidazole were slowly heated to 180° C. on an oil bath, while stirring, and allowed to remain at that temperature for about 5 minutes. The molten mass was allowed to cool, was then dissolved in dilute hydrochloric acid, and the solution was extracted once with ether. The ethereal extract solution was discarded. The acidic aqueous phase was made alkaline with 2 N sodium hydroxide and was then extracted several times with ether while salting out (common salt). The combined ethereal extracts were dried over anhydrous calcium sulfate and evaporated in vacuo, leaving 2.9 gm (63% of theory) of slightly impure reaction product, as determined by thin-layer chromatography. For further purification the product was twice stirred with ether and suction-filtered off, yielding 1.1 gm (23.9% of theory) of 7-(2-chloro-6-methyl-phenyl)-2,3-dihydro-imidazo[1,2-α]-imidazole, m.p. 105°-107° C.

Workup

  1. temperatureto cool
  2. extractionthe solution was extracted once with ether
  3. extractionThe ethereal extract solution
  4. extractionwas then extracted several times with ether while salting out (common salt)
  5. dry with materialThe combined ethereal extracts were dried over anhydrous calcium sulfate
  6. customevaporated in vacuo
  7. customleaving 2.9 gm (63% of theory) of slightly impure reaction product
  8. customFor further purification the product
  9. stirringwas twice stirred with ether
  10. filtrationsuction-filtered off

Sources & evidence

ORD record
ord-6a5e973869d94d76a821aaa2c9fe79e7
Source dataset
uspto-grants-1980_07
Patent number
US04210659

Reaction notes

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