Hydrochloric Acid → HCID 59707063, compound

HRID 221953Notes

Reaction equation

HRID 221953 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:19]=[CH:18][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[O:17])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Br[CH2:21][C:22]1[CH:27]=[CH:26][C:25]([N:28]2[C:36](=[O:37])[C:35]3[C:30](=[CH:31][CH:32]=[CH:33][CH:34]=3)[C:29]2=[O:38])=[CH:24][CH:23]=1.[Br-].Cl>O.CN(C=O)C>[C:3]([C:7]1[CH:19]=[CH:18][C:10]([CH2:11][N:12]2[CH2:16][CH2:15][N:14]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([N:28]4[C:29](=[O:38])[C:30]5[C:35](=[CH:34][CH:33]=[CH:32][CH:31]=5)[C:36]4=[O:37])=[CH:26][CH:27]=3)[C:13]2=[O:17])=[CH:9][CH:8]=1)([CH3:6])([CH3:4])[CH3:5]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 59707067HCID 59707067, compoundHCID 86619723HCID 86619723, compound

Product 1

HCID 59707063HCID 59707063, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

Sodium hydride (approximately 60% strength suspension in oil, 140 mg, approximately 3.5 mmol) was added portionwise to a solution of 1-(4-tert-butylbenzyl)imidazolidin-2-one (C) (730 mg, 3.15 mmol) in abs. DMF (15 mL) under a blanket of argon within a period of 10 min. The reaction mixture was stirred for 60 min at RT and a solution of 2-(4-bromomethylphenyl)-isoindol-1,3-dione (B) (1 g, 3.16 mmol) in abs. DMF (20 mL) was then added within a period of 60 min. The reaction mixture was stirred at RT over a period of 3 h, then heated to 100° C. over a period of 1 h, cooled, and added to a mixture of ice water (300 mL) and 2N hydrochloric acid solution in H2O (20 mL). The resulting mixture was stirred for 30 min and then extracted with DCM (4×20 mL). The combined organic phases were dried over Na2SO4 and the solvent removed in vacuo. Following purification, by column chromatography, of the residue (SiO2, cyclohexane/EtOAc 1:1), the desired product 2-{4-[3-(4-tert-butylbenzyl)-2-oxoimidazolidin-1-ylmethyl]phenyl}isoindol-1,3-dione (E) was obtained as vitreous solid matter (680 mg, 46% of theory).

Workup

  1. stirringThe reaction mixture was stirred at RT over a period of 3 h
  2. temperatureheated to 100° C. over a period of 1 h
  3. temperaturecooled
  4. stirringThe resulting mixture was stirred for 30 min
  5. extractionextracted with DCM (4×20 mL)
  6. dry with materialThe combined organic phases were dried over Na2SO4
  7. customthe solvent removed in vacuo
  8. custompurification

Sources & evidence

ORD record
ord-c1574e3eac1645d798f06c0440ccee07
Source dataset
uspto-grants-2012_06
Patent number
US08207182B2

Reaction notes

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