Sodium hydride → HCID 67126672, compound

HRID 707012Notes

Reaction equation

HRID 707012 reaction equation
[OH:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1.[H-].[Na+].[Cl:18][C:19]1[CH:20]=[C:21]([S:26]([NH2:29])(=[O:28])=[O:27])[CH:22]=[CH:23][C:24]=1F>CN(C)C=O>[Cl:18][C:19]1[CH:20]=[C:21]([S:26](=[O:28])(=[O:27])[NH2:29])[CH:22]=[CH:23][C:24]=1[O:1][CH2:2][CH:3]1[O:8][CH2:7][CH2:6][N:5]([C:9]([O:11][C:12]([CH3:15])([CH3:14])[CH3:13])=[O:10])[CH2:4]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 5201202tert-Butyl 2-(hydroxymethyl)morpholine-4-carboxylateHCID 75098833-Chloro-4-fluorobenzenesulfonamide

Product 1

HCID 67126672HCID 67126672, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of tert-butyl 2-(hydroxymethyl)morpholine-4-carboxylate (0.478 g) in anhydrous N,N-dimethylformamide (5 mL) was added sodium hydride (0.280 g). The mixture was stirred at room temperature for 30 minutes, followed by addition of 3-chloro-4-fluorobenzenesulfonamide (0.419 g). The mixture was stirred at 40° C. overnight. The reaction was quenched with water (10 mL), and the mixture was adjusted to pH 7 and extracted with ethyl acetate. The crude product was purified on a silica gel column eluting with 60% ethyl acetate in hexane to provide the title compound.

Workup

  1. stirringThe mixture was stirred at 40° C. overnight
  2. customThe reaction was quenched with water (10 mL)
  3. extractionextracted with ethyl acetate
  4. customThe crude product was purified on a silica gel column
  5. washeluting with 60% ethyl acetate in hexane

Sources & evidence

ORD record
ord-58abd69cb7734d69a7fd19fd52496862
Source dataset
uspto-grants-2015_11
Patent number
US09174982B2

Reaction notes

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