Sulfuric Acid → (S)-3-((4-Bromophenyl)amino)butanamide

HRID 2366845Notes

Reaction equation

HRID 2366845 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C@@H:9]([CH3:13])[CH2:10][C:11]#[N:12])=[CH:4][CH:3]=1.[OH:14]S(O)(=O)=O>C1(C)C=CC=CC=1.O>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([NH:8][C@@H:9]([CH3:13])[CH2:10][C:11]([NH2:12])=[O:14])=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 1118Sulfuric AcidHCID 67173345(3S)-3-[(4-bromophenyl)amino]butanenitrile

Product 1

HCID 67173762(S)-3-((4-Bromophenyl)amino)butanamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
60 °C

Procedure

(3S)-3-[(4-bromophenyl)amino]butanenitrile (for a preparation see Intermediate 32) (17.3 g, 72.4 mmol) was taken up in Toluene (500 ml) and H2SO4 (19.28 ml, 362 mmol) added. The biphasic mixture was stirred at 60° C. After two hours, only a small amount of SM remained by LCMS so the reaction was diluted with water (500 ml) and the phases separated. The aqueous phase was basified with 10N NaOH and extracted with EtOAc (2×750 ml). The combined organics were dried with Na2SO4, filtered and concentrated to yield the product as a cream solid (17.5 g). LCMS (Method B): Rt=0.77, MH+=257

Workup

  1. customthe phases separated
  2. extractionextracted with EtOAc (2×750 ml)
  3. dry with materialThe combined organics were dried with Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-c55a6635b0ce492284de95485ad441c1
Source dataset
uspto-grants-2014_04
Patent number
US08697725B2

Reaction notes

Loading…