N-[3-(bromoacetyl)phenyl]hexadecane-1-sulfonamide → Saccharin

HRID 444303Notes

Reaction equation

HRID 444303 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].[Na].C(S(NC1C=C(C(=O)CBr)C=CC=1)(=O)=O)CCCCCCCCCCCCCCC>CN(C)C=O.[Cl-].[Na+].O>[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:2])=[O:3]

Participants

5

Reactant 2

HCID 23464849N-[3-(bromoacetyl)phenyl]hexadecane-1-sulfonamideHCID 24181110Benzosulfinide sodium; Garantose sodium

Product 1

HCID 5143SaccharinYield 300.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A mixture of 4.5 g of sodium saccharin and 10 g of the product of Step B in 70 ml of dimethylformamide was stirred overnight at ambient temperature. The reaction mixture was poured in brine and icy water (about 600 ml) and the precipirated product was filtered, and recrystallized from 200 ml of methanol to give 12 g (100%) of Compound 24: mp 85.9° .

Workup

  1. filtrationicy water (about 600 ml) and the precipirated product was filtered
  2. customrecrystallized from 200 ml of methanol

Sources & evidence

ORD record
ord-511671a1512749448237ccf69a401d04
Source dataset
uspto-grants-1981_04
Patent number
US04263393

Reaction notes

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