Saccharin → HCID 25018867, compound

HRID 512017Notes

Reaction equation

HRID 512017 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][CH:24]=[C:23]([CH3:27])[CH:22]=1>CN(C=O)C>[CH3:27][C:23]1[CH:22]=[C:21]([CH:26]=[CH:25][CH:24]=1)[O:20][CH2:19][CH2:18][CH2:17][CH2:16][N:4]1[C:5](=[O:6])[C:7]2[C:12](=[CH:11][CH:10]=[CH:9][CH:8]=2)[S:1]1(=[O:2])=[O:3]

Participants

5

Reactant 3

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 5781731-(4-Bromobutoxy)-3-methylbenzene

Product 1

HCID 25018867HCID 25018867, compoundYield 55%

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)-3-methylbenzene (146 mg, 0.6 mmol) in DMF (anhydrous, 1 mL). The crude product obtained after workup was purified by flash column chromatography on silica gel (25% ethyl acetate-petroleum ether) to give 83.6 as a viscous liquid in 55% yield (95 mg).

Workup

  1. customThe crude product obtained after workup

Sources & evidence

ORD record
ord-4dab99d233b6478486dbfc84fe321709
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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