Sodium Chloride → HCID 86709273, compound

HRID 517289Notes

Reaction equation

HRID 517289 reaction equation
C1(CS(O[CH2:12][CH2:13][C@H:14]([NH:16][S:17]([CH2:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)(=[O:19])=[O:18])[CH3:15])(=O)=O)C=CC=CC=1.[Cl-:27].[Na+].CN(C)C=O>CCOC(C)=O>[Cl:27][CH2:12][CH2:13][C@H:14]([NH:16][S:17]([CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)(=[O:19])=[O:18])[CH3:15]

Participants

5

Reactant 3

HCID 5234Sodium ChlorideHCID 6228DimethylformamideHCID 86709274HCID 86709274, compound

Product 1

HCID 86709273HCID 86709273, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

To the crude (R)-3-(phenylmethylsulfonamido)butyl phenylmethanesulfonate (23.6 mmol) was added sodium chloride (984 mg, 16.8 mmol) and dimethylformamide (37 mL) and the reaction was stirred at 80° C. for 16 hours. The reaction was then diluted with EtOAc, washed with water (×2) and brine, dried with MgSO4, concentrated and purified by silica gel column chromatography (0-50% Acetone in Heptane, 216 nM) to give (R)—N-(4-chlorobutan-2-yl)-1-phenylmethanesulfonamide (1.71 g, 6.53 mmol, 58% yield over 2 steps). LCMS (ESI), m/z, 261 [M+H]+.

Workup

  1. washwashed with water (×2) and brine
  2. dry with materialdried with MgSO4
  3. concentrationconcentrated
  4. custompurified by silica gel column chromatography (0-50% Acetone in Heptane, 216 nM)

Sources & evidence

ORD record
ord-4ba0f08c49c54b7c91c6f7d32da7bb1e
Source dataset
uspto-grants-2015_08
Patent number
US09115101B2

Reaction notes

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