1,3-Dibromobutane → HCID 19855585, compound

HRID 1650005Notes

Reaction equation

HRID 1650005 reaction equation
[H-].[Na+].[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[NH:11][S:12]([CH3:15])(=[O:14])=[O:13].Br[CH2:17][CH2:18][CH:19]([Br:21])[CH3:20]>C1(C)C(C)=CC=CC=1>[CH3:3][C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[C:5]=1[N:11]([CH2:17][CH2:18][CH:19]([Br:21])[CH3:20])[S:12]([CH3:15])(=[O:14])=[O:13]

Participants

5

Reactant 3

HCID 78891,3-DibromobutaneHCID 24758Sodium hydrideHCID 686475HCID 686475, compound

Product 1

HCID 19855585HCID 19855585, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

15.5 g (0.517 moles) of a 80% sodium hydride dispersion, containing 20% of mineral oil, are added in small portions, within 0.5 hours, to a suspension of 100 g (0.5 moles) of N-(2,6-dimethylphenyl)-methanesulfonamide in 800 ml of dry xylene at room temperature, and the mixture is heated then to 130° C. within one hour. 102.5 ml (184.5 g, 0.85 moles) of 1,3-dibromo-butane are added dropwise, within 3 hours, to the mixture at 130°-135° C., and the mixture is stirred at the same temperature for additional 4 hours. Thereafter the mixture is cooled, washed twice with 200 ml of water, twice with 250 ml of 1 n aqueous sodium hydroxide solution, once with 200 ml of water, twice with 200 ml of 1 n aqueous hydrochloric acid solution and finally twice with 200 ml of water, each, dried over anhydrous magnesium sulfate, and the solvent is evaporated under reduced pressure. 109.65 g (66%) of crude 1-[N-(2,6-dimethylphenyl)-methanesulfonamido]-3-bromo-butane are obtained as a dark yellow oil; this substance can be utilized in the next step without purification.

Workup

  1. temperaturethe mixture is heated
  2. temperatureThereafter the mixture is cooled
  3. washwashed twice with 200 ml of water, twice with 250 ml of 1 n aqueous sodium hydroxide solution, once with 200 ml of water, twice with 200 ml of 1 n aqueous hydrochloric acid solution and finally twice with 200 ml of water
  4. dry with materialeach, dried over anhydrous magnesium sulfate
  5. customthe solvent is evaporated under reduced pressure

Sources & evidence

ORD record
ord-a29db8f1349a4f5b979a4461e4fee533
Source dataset
uspto-grants-1990_05
Patent number
US04922021

Reaction notes

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