Dimethylformamide → 5-(Benzo[d][1,3]dioxol-5-yl)-5-methyl-3-[4-[4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran-5-yloxy]butyl]imidazolidine-2,4-dione

HRID 552453Notes

Reaction equation

HRID 552453 reaction equation
CN(C)C=O.Br[CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]1[C:13]([CH2:29][CH2:30][CH3:31])=[C:14]2[C:18](=[CH:19][CH:20]=1)[C:17]([C:25]([F:28])([F:27])[F:26])([C:21]([F:24])([F:23])[F:22])[O:16][CH2:15]2.C(=O)([O-])[O-].[K+].[K+].[O:38]1[C:42]2[CH:43]=[CH:44][C:45]([C:47]3([CH3:54])[NH:51][C:50](=[O:52])[NH:49][C:48]3=[O:53])=[CH:46][C:41]=2[O:40][CH2:39]1>O>[O:38]1[C:42]2[CH:43]=[CH:44][C:45]([C:47]3([CH3:54])[NH:51][C:50](=[O:52])[N:49]([CH2:7][CH2:8][CH2:9][CH2:10][O:11][C:12]4[C:13]([CH2:29][CH2:30][CH3:31])=[C:14]5[C:18](=[CH:19][CH:20]=4)[C:17]([C:25]([F:28])([F:27])[F:26])([C:21]([F:24])([F:23])[F:22])[O:16][CH2:15]5)[C:48]3=[O:53])=[CH:46][C:41]=2[O:40][CH2:39]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 28298175-(2H-1,3-benzodioxol-5-yl)-5-methylimidazolidine-2,4-dioneHCID 579007815-(4-Bromobutoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran

Product 1

HCID 442412895-(Benzo[d][1,3]dioxol-5-yl)-5-methyl-3-[4-[4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran-5-yloxy]butyl]imidazolidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a N,N-Dimethylformamide (2 mL) solution of 5-(4-bromobutoxy)-4-propyl-1,1-bis(trifluoromethyl)-1,3-dihydroisobenzofuran (25 mg, 0.0557 mmol), potassium carbonate mg, 0.111 mmol) and 5-(benzo[d][1,3]dioxol-5-yl)-5-methylimidazolidine-2,4-dione (CAS: 308122-40-9:DE335993) (19.6 mg, 0.0835 mmol) were added and the mixture was stirred overnight. The reaction solution was added with water and extracted with ethyl acetate. Subsequently, the organic layer was washed with saturated saline, dried using anhydrous sodium sulfate, and concentrated in vacuum. The residue was purified by thin-layer silica-gel column chromatography (hexane:ethyl acetate=2:1) and of the title compound (30.7 mg, 92%) was obtained as colorless oil.

Workup

  1. extractionextracted with ethyl acetate
  2. washSubsequently, the organic layer was washed with saturated saline
  3. customdried
  4. concentrationconcentrated in vacuum
  5. customThe residue was purified by thin-layer silica-gel column chromatography (hexane:ethyl acetate=2:1) and of the title compound (30.7 mg, 92%)
  6. customwas obtained as colorless oil

Sources & evidence

ORD record
ord-ffd893985cdf44568a5b542a71223e0b
Source dataset
uspto-grants-2011_05
Patent number
US07951822B2

Reaction notes

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