Sodium hydride → HCID 13785478, compound

HRID 231573Notes

Reaction equation

HRID 231573 reaction equation
Cl.[CH3:2][N:3]([CH3:24])[C:4](=[O:23])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[S:14]([NH:17][CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])(=[O:16])=[O:15].[H-].[Na+].Br[CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1>CN(C=O)C>[CH3:2][N:3]([CH3:24])[C:4](=[O:23])[C:5]1[C:10]([N+:11]([O-:13])=[O:12])=[CH:9][CH:8]=[CH:7][C:6]=1[S:14]([N:17]([CH2:18][CH2:19][N:20]([CH3:22])[CH3:21])[CH2:28][CH2:29][O:30][CH:31]1[CH2:36][CH2:35][CH2:34][CH2:33][O:32]1)(=[O:15])=[O:16]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 866212-(2-Bromoethoxy)tetrahydro-2H-pyranHCID 20033757HCID 20033757, compound

Product 1

HCID 13785478HCID 13785478, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a suspension of N,N-dimethyl-2-[N-(2-dimethylaminoethyl)aminosulfonyl]-6-nitrobenzamide hydrochloride (347 mg, 0.91 mmol) in DMF (5 ml) under N2 was added 50% NaH (87 mg, 1.82 mmol). After stirring at 20-25° for 15 minutes until all of the NaH had reacted, a solution of 2-(2-bromoethoxy)tetrahydro-2H-pyran in DMF (2 ml) was added. The solution was stirred at 20-25° under N2 for 20 hours and then concentrated under reduced pressure to remove most of the DMF. The residue was partitioned between EtOAc and a saturated aqueous solution of NaCl. After drying (Na2SO4) the EtOAc extract, filtering and concentrating, the residue was chromatographed over silica gel. Elution with 7% MeOH-93% CHCl3 gave 100 mg of product.

Workup

  1. customhad reacted
  2. concentrationconcentrated under reduced pressure
  3. customto remove most of the DMF
  4. customThe residue was partitioned between EtOAc
  5. dry with materialAfter drying (Na2SO4) the EtOAc
  6. extractionextract
  7. filtrationfiltering
  8. concentrationconcentrating
  9. customthe residue was chromatographed over silica gel
  10. washElution with 7% MeOH-93% CHCl3

Sources & evidence

ORD record
ord-183c0958363140359cb0e15b0c2f3e82
Source dataset
uspto-grants-1989_07
Patent number
US04847294

Reaction notes

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