1,2-Dibromoethane → N-(2-bromoethyl)-N-(4-nitrophenyl)benzenesulfonamide

HRID 1393829Notes

Reaction equation

HRID 1393829 reaction equation
[Br:1][CH2:2][CH2:3]Br.[K].[N+:6]([C:9]1[CH:14]=[CH:13][C:12]([NH:15][S:16]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)(=[O:18])=[O:17])=[CH:11][CH:10]=1)([O-:8])=[O:7]>CN(C)C=O>[Br:1][CH2:2][CH2:3][N:15]([C:12]1[CH:13]=[CH:14][C:9]([N+:6]([O-:8])=[O:7])=[CH:10][CH:11]=1)[S:16]([C:19]1[CH:20]=[CH:21][CH:22]=[CH:23][CH:24]=1)(=[O:17])=[O:18]

Participants

5

Reactant 3

HCID 78391,2-DibromoethaneHCID 231837Benzenesulfonamide, N-(4-nitrophenyl)-HCID 5462222Potassium

Product 1

HCID 23104465N-(2-bromoethyl)-N-(4-nitrophenyl)benzenesulfonamide

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
92.5 °C

Procedure

1,2-Dibromoethane (2.26 kg, 12 mol) mixed with 4 L of dimethylformamide was brought to 80° C. 1.264 kg (4 mol) of the potassium salt of N-(4-nitrophenyl)benzenesulfonamide (5) was added in portions and the mixture was stirred at 90-95° C. for 4 hours. The resulting mixture was filtered while hot and a KBr salt was formed, which was washed with dimethylformamide. The filtrate was poured onto 20 kg of ice in 20 kg of water. A yellow precipitate formed, which was filtered off by suction, reslurried three times in hot 1N sodium hydroxide, and then reslurried in water to neutral pH. The crude product (1.2 kg wet) obtained was recrystallized from 3 L of acetic acid. This mixture was filtered while boiling and the filtrate was cooled to 20° C. A white precipitate formed, which was filtered off by suction, washed with acetic acid and then with petroleum ether, and then dried under vacuum. 773 g product with a melting temperature of 168° C. were isolated.

Workup

  1. customwas brought to 80° C
  2. filtrationThe resulting mixture was filtered while hot and a KBr salt
  3. customwas formed
  4. washwhich was washed with dimethylformamide
  5. additionThe filtrate was poured onto 20 kg of ice in 20 kg of water
  6. customA yellow precipitate formed
  7. filtrationwhich was filtered off by suction
  8. customThe crude product (1.2 kg wet) obtained
  9. customwas recrystallized from 3 L of acetic acid
  10. filtrationThis mixture was filtered
  11. temperaturethe filtrate was cooled to 20° C
  12. customA white precipitate formed
  13. filtrationwhich was filtered off by suction
  14. washwashed with acetic acid
  15. dry with materialwith petroleum ether, and then dried under vacuum

Sources & evidence

ORD record
ord-29bc8189a8a74e809132968303d3e629
Source dataset
uspto-grants-2008_03
Patent number
US07347879B2

Reaction notes

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