Water → HCID 86731078, compound

HRID 1844401Notes

Reaction equation

HRID 1844401 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([SH:9])[CH:5]=[CH:6][C:7]=1[Cl:8].Br[CH2:11][CH2:12][CH2:13][N:14]1[C:22](=[O:23])[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15]1=[O:24].C([O-])([O-])=O.[Cs+].[Cs+].O>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([S:9][CH2:11][CH2:12][CH2:13][N:14]2[C:22](=[O:23])[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[C:15]2=[O:24])[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 21611N-3-BromopropylphthalimideHCID 799643,4-Dichlorobenzenethiol

Product 1

HCID 86731078HCID 86731078, compoundYield 74.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-Dichlorobenzenethiol (500 mg, 2.79 mmol) and 2-(3-bromopropyl)isoindoline-1,3-dione (823 mg, 3.07 mmol) were stirred in DMF (2 mL) at rt. Cs2CO3 (1.64 g, 5.03 mmol) was added. The reaction mixture was stirred at rt for 14 h. H2O was added and the aqueous phase was extracted with EtOAc. The organic layer was dried over MgSO4, filtered and concentrated to give crude product. It was then triturated with ether to yield a white precipitate which was filtered and dried to give Intermediate 7A (760 mg, 2.075 mmol, 74.3% yield). LC-MS (ESI) 365.8 (M+H). RT=4.00 min (Method A).

Workup

  1. extractionthe aqueous phase was extracted with EtOAc
  2. dry with materialThe organic layer was dried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customto give crude product
  6. customIt was then triturated with ether
  7. customto yield a white precipitate which
  8. filtrationwas filtered
  9. customdried

Sources & evidence

ORD record
ord-8c8a36e64bc6495083737ea2f2c591d5
Source dataset
uspto-grants-2015_02
Patent number
US08946430B2

Reaction notes

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