Water → HCID 86731078, compound

HRID 1848375Notes

Reaction equation

HRID 1848375 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 74.6%

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, which was triturated with ether, filtered and dried to give Intermediate 10A (760 mg, 2.08 mmol, 74.0% yield). HPLC/MS (Method N) RT=4.00 min [M+1]+ 365.8.

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, which
  6. customwas triturated with ether
  7. filtrationfiltered
  8. customdried

Sources & evidence

ORD record
ord-a475d307cc074af38d6a83686224b4b2
Source dataset
uspto-grants-2015_02
Patent number
US08952180B2

Reaction notes

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