Hydrochloric Acid → HCID 15158834, compound

HRID 1087122Notes

Reaction equation

HRID 1087122 reaction equation
C([O:4][C:5]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH2:14][N:15]([CH2:29][CH3:30])[CH2:16][CH:17]([OH:28])[CH2:18][O:19][C:20]2[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=2)=[CH:7][CH:6]=1)(=O)C.C1(C)C=CC(S(O)(=O)=[O:38])=CC=1.ClC1C=CC=C(C(OO)=O)C=1.[OH-].[Na+].Cl>C(O)C>[CH2:29]([N:15]([CH2:14][CH2:13][CH2:12][S:11]([C:8]1[CH:9]=[CH:10][C:5]([OH:4])=[CH:6][CH:7]=1)=[O:38])[CH2:16][CH:17]([OH:28])[CH2:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([C:24]#[N:25])=[CH:22][CH:21]=1)[CH3:30]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 6101p-Toluenesulfonic acidHCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 15158833HCID 15158833, compound

Product 1

HCID 15158834HCID 15158834, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Conditions

Temperature
-15 °C

Procedure

A solution of 4-[3-[[3-[[4-(acetyloxy)phenyl]thio]propyl]ethylamino] -2-hydroxypropoxy]-benzonitrile (3.80 g, 8.8 mmol) and toluene-4-sulfonic acid (1.67 g, 8.8 mmol) in ethanol (100 ml) was stirred and chilled to -15 ° C. To the chilled solution was added a solution of 3-chloroperbenzoic acid (2.05 g, 8.8 mmol) in ethanol (10 ml). The solution was stirred at room temperature for 2 h. Sodium hydroxide (8.8 g, 0.22 mol) was added and the solution was stirred for 1 h. The pH was adjusted to about 7 with hydrochloric acid. After evaporation the residue was treated with 2M hydrochloric acid and washed with diethylether. The acidic aqueous layer was treated with sodium hydroxide solution to pH =9 and extracted with three portions of ethyl acetate. The combined ethyl acetate fractions were dried over sodium sulfate and evaporated. The oily residue was purified by column chromatography on silica gel. Yield: 0.9 g of the title compound.

Workup

  1. stirringthe solution was stirred for 1 h
  2. customAfter evaporation the residue
  3. additionwas treated with 2M hydrochloric acid
  4. washwashed with diethylether
  5. additionThe acidic aqueous layer was treated with sodium hydroxide solution
  6. extractionextracted with three portions of ethyl acetate
  7. dry with materialThe combined ethyl acetate fractions were dried over sodium sulfate
  8. customevaporated
  9. customThe oily residue was purified by column chromatography on silica gel

Sources & evidence

ORD record
ord-27b3256edafa4da794df101609851621
Source dataset
uspto-grants-1991_07
Patent number
US05034411

Reaction notes

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