Glycine ethyl ester, hydrochloride → 9-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-one

HRID 459893Notes

Reaction equation

HRID 459893 reaction equation
[NH2:1][C:2]1[C:15]([Cl:16])=[CH:14][CH:13]=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=O.Cl.[NH2:18][CH2:19][C:20](OCC)=[O:21]>N1C=CC=CC=1>[Cl:16][C:15]1[C:2]2[NH:1][C:20](=[O:21])[CH2:19][N:18]=[C:4]([C:6]3[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=3)[C:3]=2[CH:12]=[CH:13][CH:14]=1

Participants

4

Reactant 2

HCID 2723640Glycine ethyl ester, hydrochlorideHCID 12421745(2-Amino-3-chlorophenyl)(phenyl)methanone

Product 1

HCID 184442579-Chloro-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepin-2-oneYield 65.3%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

A solution of 2-amino-3-chlorobenzophenone (0.730 g, 3.15 mmol) and ethyl glycinate hydrochloride salt (0.660 g, 4.72 mmol) in pyridine (15 mL) was refluxed using a Dean-Stark trap to remove water. After 30 h the reaction was cooled and concentrated. The residue was dissolve in methylene chloride and washed with saturated sodium bicarbonate. The crude product was purified by chromatography (silica gel, 0–30% ethyl acetate in hexane gradient elution) to give the title compound as a solid (0.557 g). 1H NMR (500 MHz, CDCl3) δ 7.83 (br s, 1H), 7.61 (dd, J=1, 8 Hz, 1H), 7.52 (m, 2H), 7.46 (tt, J=1,8 Hz, 1H), 7.39 (t, J=8 Hz, 2H), 7.26 (m, 1H), 7.11 (t, J=8 Hz, 1H), 4.36 (br s, 2H).

Workup

  1. customto remove water
  2. temperatureAfter 30 h the reaction was cooled
  3. concentrationconcentrated
  4. dissolutionThe residue was dissolve in methylene chloride
  5. washwashed with saturated sodium bicarbonate
  6. customThe crude product was purified by chromatography (silica gel, 0–30% ethyl acetate in hexane gradient elution)

Sources & evidence

ORD record
ord-1bcf9677b3c042ef971e5cf6b7d72b02
Source dataset
uspto-grants-2007_03
Patent number
US07196079B2

Reaction notes

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