Acetic Acid → HCID 20477994, compound

HRID 904891Notes

Reaction equation

HRID 904891 reaction equation
[H-].[Na+].[CH:3]([N:6]([CH:24]([CH3:26])[CH3:25])[CH2:7][CH2:8][NH:9][CH:10]([C:16]1[CH:17]=[N:18][C:19]([CH3:23])=[CH:20][C:21]=1[CH3:22])[NH:11][C:12](=[O:15])[O:13][CH3:14])([CH3:5])[CH3:4].CI.[C:29](O)(=O)C>C1(C)C=CC=CC=1.CS(C)=O.O>[CH3:29][N:11]([CH:10]([NH:9][CH2:8][CH2:7][N:6]([CH:3]([CH3:4])[CH3:5])[CH:24]([CH3:26])[CH3:25])[C:16]1[CH:17]=[N:18][C:19]([CH3:23])=[CH:20][C:21]=1[CH3:22])[C:12](=[O:15])[O:13][CH3:14]

Participants

8

Reactant 4

HCID 176Acetic AcidHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 20477997HCID 20477997, compound

Product 1

HCID 20477994HCID 20477994, compound

Reagents, catalysts & solvents 3

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolventHCID 1140TolueneSolvent2×

Procedure

To a suspension of 50% sodium hydride in mineral oil (2.0 g, 42 mmol) in dry toluene (100 ml) under a nitrogen atmosphere is added a solution of methyl N-(2-diisopropylaminoethylamino-4,6-dimethyl-3-pyridylmethyl)carbamate (13.5 g, 40 mmol) in dry dimethyl sulfoxide (12 ml) and dry toluene (60 ml) in one portion. This mixture is stirred for one hour at room temperature and then methyliodide (2.52 ml, 40 mmol) is added dropwise. After stirring an additional three hours, acetic acid (6.0 ml) is added, followed by water. The aqueous layer is separated, washed with benzene and made basic with sodium carbonate. The product is extracted into methylene chloride, dried and evaporated to give 11.1 g of crude title A product.

Workup

  1. stirringAfter stirring an additional three hours
  2. customThe aqueous layer is separated
  3. washwashed with benzene
  4. extractionThe product is extracted into methylene chloride
  5. customdried
  6. customevaporated
  7. customto give 11.1 g of crude title A product

Sources & evidence

ORD record
ord-1f79b5889db54063bbd806a7255e3867
Source dataset
uspto-grants-1983_12
Patent number
US04420615

Reaction notes

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