Saccharin → N-(4-Phenoxy-butyl)saccharin

HRID 512014Notes

Reaction equation

HRID 512014 reaction equation
[C:1]1([CH2:7][N:8]2[C:18](=[O:19])[C:17]3[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=3)[S:9]2(=[O:11])=[O:10])[CH:6]=[CH:5]C=CC=1.S1(C2C(=CC=CC=2)C(=O)N1)(=O)=O.[H-].[Na+].[O:34](CCCCBr)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[O:34]([CH2:5][CH2:6][CH2:1][CH2:7][N:8]1[C:18](=[O:19])[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[S:9]1(=[O:10])=[O:11])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

6

Reactant 4

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 70986(4-Bromobutoxy)benzeneHCID 95841N-Benzylsaccharin

Product 1

HCID 25018611N-(4-Phenoxy-butyl)saccharinYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The synthesis was carried out analogous to the preparation of 83.1 using 82 (0.23 g, 1.25 mmol), NaH (0.030 g, 1.25 mmol) and 4-phenoxy-butyl bromide (0.115 g, 0.5 mmol) in DMF (5 mL). Purification by flash column chromatography on silica gel gave 83.2 (0.1 g, 67% yield) as a white solid (m p 92-94° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-9ec4a78b4f2340d2b1bc32eb6e15611c
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

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