Sodium hydride → N-butyl-2-[(5-hydroxypentyl)-thio]-N-methyl acetamide

HRID 1006764Notes

Reaction equation

HRID 1006764 reaction equation
[H-].[Na+].Br[CH2:4][C:5]([N:7]([CH2:9][CH2:10][CH2:11][CH3:12])[CH3:8])=[O:6].[SH:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19].[Cl-].[NH4+]>O1CCCC1>[CH2:9]([N:7]([CH3:8])[C:5](=[O:6])[CH2:4][S:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][OH:19])[CH2:10][CH2:11][CH3:12]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 5342591-Pentanol, 5-mercapto-HCID 10798390Acetamide, 2-bromo-N-butyl-N-methyl-

Product 1

HCID 85637568N-butyl-2-[(5-hydroxypentyl)-thio]-N-methyl acetamideYield 76.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1.4 g of sodium hydride at 50% in oil and 6 g of bromo N-butyl-N-methyl acetamide of Step A of Preparation B of Example 78 were added to a solution of 3.36 g of the product of Step A in 45 ml of tetrahydrofuran under a nitrogen atmosphere. The mixture was stirred for 2 hours at ambient temperature and poured into an ammonium chloride solution and extracted with ethyl acetate. The extracts were washed and evaporated to dryness under reduced pressure. The 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8) to obtain 5.27 g of the expected product.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe extracts were washed
  3. customevaporated to dryness under reduced pressure
  4. customThe 10 g of residue were chromatographed on silica (eluant: cyclohexane-ethyl acetate 2-8)

Sources & evidence

ORD record
ord-0693ffd8aeb2442e945572b7a921db76
Source dataset
uspto-grants-2004_09
Patent number
US06790971B1

Reaction notes

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