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Benzyl Bromide → 5-(Dibenzylamino)-2-benzofuran-1(3H)-one

HRID 1829035
Notes
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Reaction equation

HRID 1829035 reaction equation
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]2[C:6](=[O:9])[O:7][CH2:8][C:4]=2[CH:3]=1.[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.[CH:20](N(C(C)C)CC)([CH3:22])[CH3:21].[CH2:29]1[CH2:33]O[CH2:31][CH2:30]1>>[CH2:12]([N:1]([CH2:31][C:30]1[CH:22]=[CH:20][CH:21]=[CH:33][CH:29]=1)[C:2]1[CH:3]=[C:4]2[C:5](=[CH:10][CH:11]=1)[C:6](=[O:9])[O:7][CH2:8]2)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 4

HCID 7498Benzyl BromideHCID 8028TetrahydrofuranHCID 81531DiisopropylethylamineHCID 7206695-Aminophthalide

Product 1

HCID 220614885-(Dibenzylamino)-2-benzofuran-1(3H)-oneYield 31%

Conditions

Temperature
50 °C

Procedure

A mixture of 5-amino-2-benzofuran-1(3H)-one (100 mg, 0.67 mmol), benzyl bromide (319 μl, 2.68 mmol), and diisopropylethylamine (350 μl, 2.01 mmol) in THF (2.0 ml) was heated at 50° C. for 65 hours. The reaction was partitioned between water and EtOAc. The organic layer was washed with water, brine, dried with Na2SO4 and rotary evaporated. The yellow oil was triturated at room temperature with 10% EtOAc/hexane and then chromatographed (20% to 40% EtOAc/hexane gradient) to give 5-dibenzylamino-3H-isobenzofuran-1-one as a white solid (136 mg, 31%).

Workup

  1. customThe reaction was partitioned between water and EtOAc
  2. washThe organic layer was washed with water, brine
  3. dry with materialdried with Na2SO4 and rotary evaporated
  4. customThe yellow oil was triturated at room temperature with 10% EtOAc/hexane
  5. customchromatographed (20% to 40% EtOAc/hexane gradient)

Sources & evidence

ORD record
ord-e52d2174dfd34d4b80a014c407536b9c
Source dataset
uspto-grants-2006_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07060844B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes