Propargyl bromide → HCID 14457166, compound

HRID 1085207Notes

Reaction equation

HRID 1085207 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+].Br[CH2:15][C:16]#[CH:17]>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[O:1]=[C:2]1[N:6]([CH2:17][C:16]#[CH:15])[CH:5]=[C:4]([C:7]([O:9][CH2:10][CH3:11])=[O:8])[S:3]1

Participants

6

Reactant 3

HCID 7842Propargyl bromideHCID 14797Potassium HydroxideHCID 14457167HCID 14457167, compound

Product 1

HCID 14457166HCID 14457166, compound

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 1140TolueneSolvent

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-propyne 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-66a19989a7d04eb99f52703e0c477e2c
Source dataset
uspto-grants-1991_04
Patent number
US05008281

Reaction notes

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