Dichloromethane → HCID 86660158, compound

HRID 1615029Notes

Reaction equation

HRID 1615029 reaction equation
[CH2:1]([NH:3][S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])(=[O:6])=[O:5])[CH3:2].[Br:16][CH2:17][CH2:18][CH2:19]Br.[H-].[Na+].C(Cl)Cl>CN(C=O)C>[Br:16][CH2:17][CH2:18][CH2:19][N:3]([CH2:1][CH3:2])[S:4]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=1[N+:13]([O-:15])=[O:14])(=[O:5])=[O:6]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 80011,3-DibromopropaneHCID 24758Sodium hydrideHCID 744706N-ethyl-2-nitrobenzenesulfonamide

Product 1

HCID 86660158HCID 86660158, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Compound 63 (7.8 g, 33.9 mmol) was dissolved in DMF (100 mL). 1,3-Dibromopropane (35 mL, 343.0 mmol) and then in portions NaH (2.7 g, 67.5 mmol) were added, whereupon the temperature rose to 50-60° C. The reaction mixture was stirred at this temperature for 1 h (TLC monitoring, CH2Cl2), carefully poured into ice/water mixture, and extracted with ethyl acetate. The extract was evaporated. The residue washed with hexane to remove the 1,3-dibromopropane. Compound 64 (9.7 g, 82%) was obtained as a viscous yellow oil.

Workup

  1. customrose to 50-60° C
  2. extractionextracted with ethyl acetate
  3. customThe extract was evaporated
  4. washThe residue washed with hexane
  5. customto remove the 1,3-dibromopropane

Sources & evidence

ORD record
ord-a14f372bfcfd477fb591ed98f07330c4
Source dataset
uspto-grants-2014_07
Patent number
US08765738B2

Reaction notes

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