Dichloromethane → N-(3-bromopropyl)-2-nitro-N-propylbenzenesulfonamide

HRID 1615015Notes

Reaction equation

HRID 1615015 reaction equation
[Br:1][CH2:2][CH2:3][CH2:4]Br.[N+:6]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[S:15]([NH:18][CH2:19][CH2:20][CH3:21])(=[O:17])=[O:16])([O-:8])=[O:7].[H-].[Na+].C(Cl)Cl>CN(C=O)C>[Br:1][CH2:2][CH2:3][CH2:4][N:18]([CH2:19][CH2:20][CH3:21])[S:15]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N+:6]([O-:8])=[O:7])(=[O:16])=[O:17]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 23033002-Nitro-N-propylbenzenesulfonamide

Product 1

HCID 67368759N-(3-bromopropyl)-2-nitro-N-propylbenzenesulfonamideYield 62.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1,3-Dibromopropane (8.5 mL, 82.0 mmol, 10 eq.) was added to a solution of compound 49 (2.0 g, 8.2 mmol) in DMF (20 mL). Then NaH (0.6 g, 15.0 mmol) was added in portions. The temperature rose to 50-60° C. The mixture was stirred at this temperature for 20 min (TLC monitoring, eluent: CH2Cl2). Then the mixture was carefully poured into ice. The product was extracted with ethyl acetate, and the extract was evaporated. The residue was washed from 1,3-dibromopropane with hexane. The resulting product was dissolved in CH2Cl2 and purified on a short thick column with silica gel, eluent: hexane-CH2Cl2 100:0→0:100. Compound 50 (1.87 g, 62%) was isolated as rapidly crystallizable oil.

Workup

  1. customrose to 50-60° C
  2. additionThen the mixture was carefully poured into ice
  3. extractionThe product was extracted with ethyl acetate
  4. customthe extract was evaporated
  5. washThe residue was washed from 1,3-dibromopropane with hexane
  6. dissolutionThe resulting product was dissolved in CH2Cl2
  7. custompurified on a short thick column with silica gel, eluent

Sources & evidence

ORD record
ord-25d38bffd8324954bab96c082e29947c
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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