Acetic Acid → HCID 22219473, compound

HRID 1793945Notes

Reaction equation

HRID 1793945 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][NH:10][S:11]([C:14]2[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=2[O:22][CH3:23])(=[O:13])=[O:12])=[C:4]([N+:24]([O-])=O)[CH:3]=1.C(O)(=O)C.Cl.N>O1CCCC1.[Zn]>[NH2:24][C:4]1[CH:3]=[C:2]([Br:1])[CH:7]=[CH:6][C:5]=1[CH2:8][CH2:9][NH:10][S:11]([C:14]1[CH:19]=[C:18]([C:20]#[N:21])[CH:17]=[CH:16][C:15]=1[O:22][CH3:23])(=[O:13])=[O:12]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 222AmmoniaHCID 313Hydrochloric AcidHCID 22219491HCID 22219491, compound

Product 1

HCID 22219473HCID 22219473, compoundYield 101.5%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 5.9 g of N-[2-(4-bromo-2-nitrophenyl)ethyl]-5-cyano-2-methoxybenzenesulfonamide and 46 mL of acetic acid in 67 mL of tetrahydrofuran were added successively 2.23 mL of concentrated hydrochloric acid and 8.76 g of zinc under ice-cooling. After the mixture was stirred at room temperature for an hour, and to the reaction mixture was added 25% aqueous ammonia solution to alkalify. After the mixture was extracted with ethyl acetate, the organic layer was washed with brine, and dried over anhydrous magnesium sulfate. The solvent was removed under reduced pressure to give 5.58 g of N-[2-(2-amino-4-bromophenyl)ethyl]-5-cyano-2-methoxybenzenesulfonamide.

Workup

  1. temperaturecooling
  2. extractionAfter the mixture was extracted with ethyl acetate
  3. washthe organic layer was washed with brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was removed under reduced pressure

Sources & evidence

ORD record
ord-6a574dd0c9304f4aaf389acbf3f558c7
Source dataset
uspto-grants-2006_04
Patent number
US07022689B2

Reaction notes

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