Saccharin → N-[4-(4-Benzyloxy-phenoxy)-butyl]saccharin

HRID 512015Notes

Reaction equation

HRID 512015 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+].[CH2:34]([O:41][C:42]1[CH:53]=[CH:52][C:45]([O:46]CCCCBr)=[CH:44][CH:43]=1)[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>CN(C=O)C>[CH2:34]([O:41][C:42]1[CH:43]=[CH:44][C:45]([O:46][CH2:5][CH2:6][CH2:1][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:10])=[O:11])=[CH:52][CH:53]=1)[C:35]1[CH:36]=[CH:37][CH:38]=[CH:39][CH:40]=1

Participants

6

Reactant 4

HCID 5143SaccharinHCID 24758Sodium hydrideHCID 95841N-BenzylsaccharinHCID 13338479HCID 13338479, compound

Product 1

HCID 25018865N-[4-(4-Benzyloxy-phenoxy)-butyl]saccharinYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The synthesis was carried out analogous to the preparation of 83.1 using 82 (0.307 g, 1.5 mmol), NaH (0.036 g, 1.5 mmol) and 4-(4-benzyloxy-phenoxy)-butyl bromide (0.2 g, 0.6 mmol) in DMF (5 mL). Purification by flash column chromatography on silica gel gave 83.3 (0.150 g, 66% yield) as a white solid (m p 82-84° C.).

Workup

  1. customPurification by flash column chromatography on silica gel

Sources & evidence

ORD record
ord-446bca1faf704ae4ad6a34285b612b54
Source dataset
uspto-grants-2015_08
Patent number
US09102622B2

Reaction notes

Loading…