Ammonium Chloride → 2-(Benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester

HRID 2222968Notes

Reaction equation

HRID 2222968 reaction equation
[CH2:1]([O:3][C:4](=[O:20])[CH2:5][N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH3:2].CC(C)([O-])C.[K+].Br[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=1.[Cl-].[NH4+]>O1CCCC1.[Cl-].[Na+].O.O>[CH2:1]([O:3][C:4](=[O:20])[CH:5]([N:6]=[C:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)[C:8]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=1)[CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([N+:35]([O-:37])=[O:36])[CH:30]=1)[CH3:2]

Participants

8

Reactant 4

HCID 25517Ammonium ChlorideHCID 77568Benzene, 1-(bromomethyl)-3-nitro-HCID 319508Ethyl 2-(diphenylmethyleneamino)acetateHCID 23665647Potassium tert-butoxide

Product 1

HCID 862288012-(Benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent3×HCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of (benzhydrylidene-amino)-acetic acid ethyl ester (2.84 g, 10.4 mmol) in anhydrous tetrahydrofuran (15 mL) at −78° C. under an atmosphere of argon was added a 1 M solution of potassium tert-butoxide in tetrahydrofuran (11 mL, 11 mmol) to form a red/orange solution. After stirring at −78° C. for 15 minutes a solution of 1-bromomethyl-3-nitro-benzene (2.14 g, 9.7 mmol) in tetrahydrofuran (20 mL) was added and the reaction mixture left to warm slowly to ambient temperature and stir for 16 hours. To the reaction mixture was added saturated aqueous ammonium chloride (20 mL), the mixture was poured into water (100 mL), diluted with brine (50 mL) and extracted with ethyl acetate (3×50 mL). The combined organic extracts were washed with brine (2×50 mL), dried over sodium sulfate and concentrated in vacuo to give crude 2-(benzhydrylidene-amino)-3-(3-nitro-phenyl)-propionic acid ethyl ester as a red/brown viscous oil which was used without further purification (4.1 g, ≈100%).

Workup

  1. customto form a red/orange solution
  2. additionwas added
  3. waitthe reaction mixture left
  4. extractionextracted with ethyl acetate (3×50 mL)
  5. washThe combined organic extracts were washed with brine (2×50 mL)
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-8d47822b81e84265b4584d1334e1b131
Source dataset
uspto-grants-2008_05
Patent number
US07371869B2

Reaction notes

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