Water → HCID 15079924, compound

HRID 477394Notes

Reaction equation

HRID 477394 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([NH:16][C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)[N:3]=1.[CH3:24]I.O>[Br-].C([P+](CCCC)(CCCC)CCCC)CCC.[OH-].[Na+].C1C=CC=CC=1>[CH3:8][C:6]1[CH:7]=[C:2]([CH3:1])[N:3]=[C:4]([S:9][C:10]2[CH:15]=[CH:14][C:13]([N:16]([CH3:24])[C:17](=[O:23])[CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:12][CH:11]=2)[N:5]=1

Participants

7

Reactant 3

HCID 962WaterHCID 6328Methyl iodideHCID 15079923HCID 15079923, compound

Product 1

HCID 15079924HCID 15079924, compoundYield 83.9%

Reagents, catalysts & solvents 3

HCID 76564Tetrabutylphosphonium bromideCatalystHCID 241BenzeneSolventHCID 14798Sodium HydroxideSolvent

Procedure

Four grams N-[4-[(4,6-dimethylpyrimidin-2-yl)thio]phenyl]hexanamide, 3.4 g methyl iodide and 0.4 g tetrabutylphosphonium bromide was dissolved in a mixture of 10 ml 50% NaOH and 50 ml benzene. This was stirred vigorously at room temperature for 72 hours. Fifty milliliters water was then added and the benzene layer was separated off. The benzene solution was washed with 4×100 ml water then dried over Na2SO4. The solvent was evaporated giving 3.5 g dark brown oil. The oil was chromatographed on silica gel eluted with 50% ethyl acetate/hexanes giving 2.5 g yellow oil which slowly crystallized. Melting point of the resulting pale yellow wolid was 61°-63° C. The structure was confirmed by infrared, nuclear magnetic resonance and mass spectral analysis as that of the desired product, N-[4[(4,6-dimethylpyrimidin-2-yl)thio]phenyl]-N-methylhexanamide.

Workup

  1. customthe benzene layer was separated off
  2. washThe benzene solution was washed with 4×100 ml water
  3. dry with materialthen dried over Na2SO4
  4. customThe solvent was evaporated

Sources & evidence

ORD record
ord-0f37a8142f5b4e599130f56cf0da0f1b
Source dataset
uspto-grants-1989_12
Patent number
US04888047

Reaction notes

Loading…