HCID 12900038, compound → HCID 12900039, compound

HRID 1278382Notes

Reaction equation

HRID 1278382 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. extractionextracted with 3×600 ml of methylene chloride
  6. dry with materialdried over sodium sulfate
  7. filtrationThe solution was filtered free
  8. customof drying agent
  9. concentrationthe filtrate concentrated to dryness
  10. customgiving an oil
  11. customThe oil was crystallized from 180 ml of ether
  12. customThe resulting crystals were collected
  13. customdried
  14. customto give

Sources & evidence

ORD record
ord-19b32d1d97714d42bd995cb9db9d717d
Source dataset
uspto-grants-1981_07
Patent number
US04281142

Reaction notes

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