1-Bromo-3-chloropropane → HCID 14407181, compound

HRID 1709830Notes

Reaction equation

HRID 1709830 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:13][CH2:14][CH2:15][Cl:16].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[Cl:16][CH2:15][CH2:14][CH2:13][O:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([NH2:11])(=[O:9])=[O:10])=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 80061-Bromo-3-chloropropaneHCID 11430Potassium CarbonateHCID 74093p-Hydroxybenzenesulfonamide

Product 1

HCID 14407181HCID 14407181, compoundYield 89.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 25 g (0.144 mole) of p-hydroxybenzenesulfonamide, 45.5 g (0.289 mole) of 1-bromo-3-chloropropane and 59.7 g (0.432 mole) of anhydrous potassium carbonate in 500 ml of acetone was heated at reflux for 24 hr. The mixture was cooled, filtered and the filtrate concentrated under vacuum pump pressure at 90° C. to give 32.2 g of tan gum as residue. The gum was purified by column chromatography on 600 g of silica gel. Fractions containing the title compound eluted with 8% acetone in benzene were combined and concentrated under reduced pressure to yield 12.2 g (34%) of white solid, m.p. 106°-107.5° C. on recrystallization from 2-propanol.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hr
  3. temperatureThe mixture was cooled
  4. filtrationfiltered
  5. concentrationthe filtrate concentrated under vacuum pump pressure at 90° C.

Sources & evidence

ORD record
ord-a5b6794ee5154608ad91b14721fe232a
Source dataset
uspto-grants-1990_08
Patent number
US04950674

Reaction notes

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