Saccharin → HCID 2923625, compound

HRID 512018Notes

Reaction equation

HRID 512018 reaction equation
[S:1]1([C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[C:5](=[O:6])[NH:4]1)(=[O:3])=[O:2].[H-].[Na+].Br[CH2:16][CH2:17][CH2:18][CH2:19][O:20][C:21]1[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][CH:22]=1>CN(C=O)C>[Cl:27][C:24]1[CH:25]=[CH:26][C:21]([O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:4]2[C:5](=[O:6])[C:7]3[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=3)[S:1]2(=[O:2])=[O:3])=[CH:22][CH:23]=1

Participants

5

Reactant 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 27349341-(4-bromobutoxy)-4-chlorobenzene

Product 1

HCID 2923625HCID 2923625, compoundYield 57%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

The title compound was synthesized analogously to 83.8 (see experimental below), using a solution of saccharin (92 mg, 0.5 mmol) in anhydrous DMF (4 mL), NaH (60% dispersion in mineral oil, 21 mg, 0.52 mmol) and a solution of 1-(4-bromobutoxy)-4-chlorobenzene (158 mg, 0.6 mmol) in anhydrous DMF (1 mL). The crude product obtained after workup was purified by flash column chromatography on silica gel (25% ethyl acetate-petroleum ether) to give 83.7 as a white solid (m p 85-88° C.) in 57% yield (104 mg).

Workup

  1. customThe crude product obtained after workup

Sources & evidence

ORD record
ord-416d4169a6f6499783ff48bfd90f5a8d
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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