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Sodium hydride → N-Ethyl-N-[6-(((4-methoxypyridin-2-yl)methyl)oxy)-2,2-dimethylchroman-4-yl]methanesulfonamide

HRID 567064
Notes
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Reaction equation

HRID 567064 reaction equation
[CH3:1][C:2]1([CH3:20])[CH2:11][CH:10]([N:12]([CH2:17][CH3:18])[S:13]([CH3:16])(=[O:15])=[O:14])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([OH:19])[CH:8]=2)[O:3]1.[H-].[Na+].Cl.[CH3:24][O:25][C:26]1[CH:31]=[CH:30][N:29]=[C:28]([CH2:32]Cl)[CH:27]=1>CC(N(C)C)=O>[CH2:17]([N:12]([CH:10]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([O:19][CH2:32][C:28]3[CH:27]=[C:26]([O:25][CH3:24])[CH:31]=[CH:30][N:29]=3)[CH:8]=2)[O:3][C:2]([CH3:1])([CH3:20])[CH2:11]1)[S:13]([CH3:16])(=[O:15])=[O:14])[CH3:18]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 139233682-(Chloromethyl)-4-methoxypyridine hydrochlorideHCID 17786837N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide

Product 1

HCID 9802243N-Ethyl-N-[6-(((4-methoxypyridin-2-yl)methyl)oxy)-2,2-dimethylchroman-4-yl]methanesulfonamide

Reagents, catalysts & solvents 1

HCID 31374
Dimethylacetamide
Solvent
2×

Conditions

Temperature
75 °C

Procedure

0.58 g (1.9 mmol) of N-[2,2-dimethyl-6-hydroxychroman-4-yl]-N-ethyl-methanesulfonamide (Example 1g) was stirred at 50° C. for 30 min with 0.15 g (5 mmol) of NaH (80%) in 40 ml of DMA. A solution of 0.4 g (2 mmol) of 4-methoxy-2-chloromethylpyridine hydrochloride in 5 ml of DMA was then added dropwise and the mixture was heated to 75° C. for 2 h. After reaction was complete, it was concentrated in vac., the residue was treated with ice water, the mixture was extracted with EA, the extract was dried and concentrated, and the residue was crystallized using diisopropyl ether. 0.5 g was obtained, m.p. 87-89° C.

Workup

  1. customAfter reaction
  2. concentrationit was concentrated in vac
  3. addition, the residue was treated with ice water
  4. extractionthe mixture was extracted with EA
  5. customthe extract was dried
  6. concentrationconcentrated
  7. customthe residue was crystallized
  8. custom0.5 g was obtained

Sources & evidence

ORD record
ord-ad04de4d3e4840b5810b71797efbac5b
Source dataset
uspto-grants-2001_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06177449B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes