Toluene → HCID 14457166, compound

HRID 1650742Notes

Reaction equation

HRID 1650742 reaction equation
[O:1]=[C:2]1[NH:6][CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:3]1.[OH-].[K+].[C:14]1(C)[CH:19]=CC=C[CH:15]=1>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]=[C:2]1[N:6]([CH2:19][C:14]#[CH:15])[CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:3]1

Participants

5

Reactant 3

HCID 1140TolueneHCID 14797Potassium HydroxideHCID 14457167HCID 14457167, compound

Product 1

HCID 14457166HCID 14457166, compound

Reagents, catalysts & solvents 1

HCID 74236Tetrabutylammonium BromideCatalyst

Procedure

A mixture of 8.65 g of the product of Step A in 130 ml of toluene, 2.8 g of potassium hydroxide, 4.5 ml of 3-bromo-1-propane and 1.66 g of tetrabutyl ammonium bromide was heated to 95 C and stirred for 3 hours. The mixture was decanted, washed with N sodium hydroxide, with N hydrochloric acid and with water saturated with sodium chloride, dried and brought to dryness. The residue was chromatographed and elution with a hexane-chloroform-acetone mixture (70-15-15) yielded 4.74 g of the expected product melting at 70° to 71° C.

Workup

  1. temperaturewas heated to 95 C
  2. customThe mixture was decanted
  3. washwashed with N sodium hydroxide, with N hydrochloric acid and with water saturated with sodium chloride
  4. customdried
  5. customThe residue was chromatographed
  6. washelution with a hexane-chloroform-acetone mixture (70-15-15)

Sources & evidence

ORD record
ord-67685c8aff9b4fadb2c50a41779bcb13
Source dataset
uspto-grants-1990_05
Patent number
US04925862

Reaction notes

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