1,4-Dibromobutane → HCID 15611140, compound

HRID 1091140Notes

Reaction equation

HRID 1091140 reaction equation
[OH:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)=[O:5].C(=O)([O-])[O-].[K+].[K+].[Br:26][CH2:27][CH2:28][CH2:29][CH2:30]Br>CC(C)=O>[Br:26][CH2:27][CH2:28][CH2:29][CH2:30][O:1][C:2]1[CH:19]=[CH:18][CH:17]=[CH:16][C:3]=1[C:4]([NH:6][C:7]1[CH:15]=[CH:14][CH:13]=[C:12]2[C:8]=1[CH:9]=[CH:10][NH:11]2)=[O:5]

Participants

5

Reactant 3

HCID 80561,4-DibromobutaneHCID 11430Potassium CarbonateHCID 13787428HCID 13787428, compound

Product 1

HCID 15611140HCID 15611140, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A suspension of 7.5 g of 2-hydroxy-N-(1H-indol-4-yl)benzamide and 8.28 g of potassium carbonate in 150 ml of acetone was refluxed for 75 minutes with 18 ml of 1,4-dibromobutane and the mixture was cooled. The precipitate was filtered off and rinsed with acetone and the filtrate was evaporated to dryness. The residue was purified by chromatography over silica (eluant: methylene chloride/ethyl acetate 9:1), followed by crystallization from ethyl acetate to obtain 2-(4-bromobutoxy) -N-(1H-indol-4-yl)benzamide melting at 135° C.

Workup

  1. temperaturethe mixture was cooled
  2. filtrationThe precipitate was filtered off
  3. washrinsed with acetone
  4. customthe filtrate was evaporated to dryness
  5. customThe residue was purified by chromatography over silica (eluant: methylene chloride/ethyl acetate 9:1)
  6. customfollowed by crystallization from ethyl acetate

Sources & evidence

ORD record
ord-d05ab429681244a79080cd6f2c8013b9
Source dataset
uspto-grants-1992_01
Patent number
US05084455

Reaction notes

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