Acetyl chloride → HCID 15158833, compound

HRID 1087121Notes

Reaction equation

HRID 1087121 reaction equation
[OH-].[Na+].[CH2:3]([N:5]([CH2:19][CH2:20][CH2:21][S:22][C:23]1[CH:28]=[CH:27][C:26]([OH:29])=[CH:25][CH:24]=1)[CH2:6][CH:7]([OH:18])[CH2:8][O:9][C:10]1[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=1)[CH3:4].[C:30](Cl)(=[O:32])[CH3:31]>S([O-])(O)(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.O1CCOCC1>[C:30]([O:29][C:26]1[CH:25]=[CH:24][C:23]([S:22][CH2:21][CH2:20][CH2:19][N:5]([CH2:3][CH3:4])[CH2:6][CH:7]([OH:18])[CH2:8][O:9][C:10]2[CH:17]=[CH:16][C:13]([C:14]#[N:15])=[CH:12][CH:11]=2)=[CH:28][CH:27]=1)(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 6367Acetyl chlorideHCID 14798Sodium HydroxideHCID 15158820HCID 15158820, compound

Product 1

HCID 15158833HCID 15158833, compound

Reagents, catalysts & solvents 2

HCID 94433Tetrabutylammonium hydrogen sulfateCatalystHCID 312751,4-DioxaneSolvent

Procedure

To a solution of sodium hydroxide (0.9 g in 25 ml dioxan) was added 4-[3-[ethyl[3-[(4-hydroxyphenyl)thio]propyl]amino]-2-hydroxypropoxy]-benzonitrile (3.4 g, 8.8 mmol) and tetrabutylammonium hydrogen sulphate. To the solution was added dropwise acetylchloride (0.78 g, 10 mmol) dissolved in dioxan (10 ml). The solution was stirred at room temperature for 2 h. After filtration and evaporation the residue was dissolved in methylene chloride, treated with charcoal and filtered through Celite. The solvent was evaporated. The yield of the title compound was 3.8 g.

Workup

  1. filtrationAfter filtration and evaporation the residue
  2. dissolutionwas dissolved in methylene chloride
  3. additiontreated with charcoal
  4. filtrationfiltered through Celite
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-1593a147433145b38897da08e2d16745
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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