1,3-Dibromopropane → HCID 22768839, compound

HRID 1764665Notes

Reaction equation

HRID 1764665 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]=2[C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:10])=[O:9])=[CH:4][CH:3]=1.Br[CH2:27][CH2:28][CH2:29]Br.C(=O)([O-])[O-].[K+].[K+].[CH2:37]([NH:41][CH2:42][CH2:43][CH2:44][CH3:45])[CH2:38][CH2:39][CH3:40]>C(O)C.CC(C)=O>[CH2:37]([N:41]([CH2:42][CH2:43][CH2:44][CH3:45])[CH2:27][CH2:28][CH2:29][O:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([C:11]2[C:15]3[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=3[O:13][C:12]=2[C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:10])=[O:9])=[CH:6][CH:7]=1)[CH2:38][CH2:39][CH3:40]

Participants

7

Reactant 4

HCID 80011,3-Dibromopropane2×HCID 8148DibutylamineHCID 11430Potassium Carbonate2×HCID 22768860HCID 22768860, compound

Product 1

HCID 22768839HCID 22768839, compound

Reagents, catalysts & solvents 2

HCID 180AcetoneSolvent2×HCID 702EthanolSolvent2×

Procedure

To a solution of 0.85 g. (0.0024 mol.) of 3-(4-hydroxyphenylsulfonyl)-2-phenylbenzofuran in 25 ml. of dry acetone was added 0.96 g. (0.0048 mol.) of 1,3-dibromopropane and 0.66 g. (0.0048 mol.) of potassium carbonate. The mixture was refluxed for ca. 12 hours, then an additional 0.4 g. of 1,3-dibromopropane, 0.3 g. of potassium carbonate and 25 ml. of dry acetone were added and the mixture was refluxed for 5 hours. The reaction mixture was filtered and the solvent was removed in vacuo to give a residue which was dissolved in 2-4 ml. of ethanol to which 22-24 ml. of freshly distilled di-n-butylamine was added. The mixture was heated at 130° for 4 hours, then cooled and diluted with ethanol. The solvent and excess amine were removed by evaporation to give 0.23 g. of the title compound.

Workup

  1. temperatureThe mixture was refluxed for ca. 12 hours
  2. temperaturethe mixture was refluxed for 5 hours
  3. filtrationThe reaction mixture was filtered
  4. customthe solvent was removed in vacuo
  5. customto give a residue which
  6. dissolutionwas dissolved in 2-4 ml
  7. temperatureThe mixture was heated at 130° for 4 hours
  8. temperaturecooled
  9. customThe solvent and excess amine were removed by evaporation
  10. customto give 0.23 g

Sources & evidence

ORD record
ord-1d2078a83b194665bad2ffd971bf55d7
Source dataset
uspto-grants-1978_09
Patent number
US04117128

Reaction notes

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