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

HRID 2201325Notes

Reaction equation

HRID 2201325 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 12) (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-9c98625d36b8424eaed5a00e7e7acf5c
Source dataset
uspto-grants-2016_06
Patent number
US09360482B2

Reaction notes

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