HCID 12900038, compound → HCID 12900039, compound

HRID 1701573Notes

Reaction equation

HRID 1701573 reaction equation
Cl[CH2:2][C:3]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:6]([CH3:23])=[N:5][CH:4]=1.CC(C)([O-])C.[K+].[C:30]1(=[O:40])[NH:34][C:33](=[O:35])[C:32]2=[CH:36][CH:37]=[CH:38][CH:39]=[C:31]12.[K]>O1CCCC1>[CH3:23][C:6]1[N:7]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:9]=2[CH2:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[F:22])[C:3]([CH2:2][N:34]2[C:30](=[O:40])[C:31]3[C:32](=[CH:36][CH:37]=[CH:38][CH:39]=3)[C:33]2=[O:35])=[CH:4][N:5]=1

Participants

5

Reactant 3

HCID 12900038HCID 12900038, compoundHCID 23665647Potassium tert-butoxideHCID 24194345Phthalimide potassium salt

Product 1

HCID 12900039HCID 12900039, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
10 °C

Procedure

To a suspension of 89.4 g (0.232 mole) of 5-(chloromethyl)-2-methyl-1-[4-chloro-2-(2-fluorobenzyl)phenyl]-1H-imidazole in 900 ml of tetrahydrofuran cooled to 10° C. was added 26.2 g (0.232 mole) of potassium t-butoxide. The temperature was maintained at 20° C. by means of an ice water bath during this addition. The bath was removed. To this mixture was added 51.5 g (0.278 mole) of potassium phthalimide. The reaction mixture was stirred under reflux for 2 hr. The mixture was cooled to room temperature and poured onto 1.2 l. of ice-water and extracted with 3×600 ml of methylene chloride. The organic phases were combined and dried over sodium sulfate. The solution was filtered free of drying agent and the filtrate concentrated to dryness giving an oil. The oil was crystallized from 180 ml of ether. The resulting crystals were collected and dried to give end product of m.p. 152°-156° C.

Workup

  1. temperatureThe temperature was maintained at 20° C. by means of an ice water bath during this addition
  2. customThe bath was removed
  3. temperatureunder reflux for 2 hr
  4. temperatureThe mixture was cooled to room temperature
  5. additionpoured onto 1.2 l
  6. extractionof ice-water and extracted with 3×600 ml of methylene chloride
  7. dry with materialdried over sodium sulfate
  8. filtrationThe solution was filtered free
  9. customof drying agent
  10. concentrationthe filtrate concentrated to dryness
  11. customgiving an oil
  12. customThe oil was crystallized from 180 ml of ether
  13. customThe resulting crystals were collected
  14. customdried
  15. customto give

Sources & evidence

ORD record
ord-1ee495aff69b4e9d8c5ab6c2f08ee41f
Source dataset
uspto-grants-1980_03
Patent number
US04194049

Reaction notes

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