Ammonia → HCID 21501536, compound

HRID 1729851Notes

Reaction equation

HRID 1729851 reaction equation
[CH:1]([O:3][CH2:4][CH2:5][NH:6][C:7]1[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=1[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)=O)=[CH2:2].[O:22]1[C:26](=O)[CH2:25][NH:24]C1=O.Cl.N>C(Cl)Cl.O>[ClH:21].[CH:1]([O:3][CH2:4][CH2:5][N:6]1[C:7]2[CH:20]=[CH:19][C:18]([Cl:21])=[CH:17][C:8]=2[C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:24][CH2:25][C:26]1=[O:22])=[CH2:2]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 75136Oxazolidine-2,5-dioneHCID 21501540(5-Chloro-2-{[2-(ethenyloxy)ethyl]amino}phenyl)(phenyl)methanone

Product 1

HCID 21501536HCID 21501536, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.3g of 2-(β-vinyloxyethyl)amino-5-chlorobenzophenone in 20 ml of dry methylene chloride is added 0.27g of oxazolidin-2,5-dione. To the mixture is added 20 ml of etheral hydrogen chloride under cooling. The mixture is allowed to stand at room temperature with occasional stirring. The reaction mixture is poured into water, basified with aqueous ammonia and extracted with methylene chloride. The extracts are combined and dried over sodium sulfate, and the solvent is removed under reduced pressure. The residue is dissolved in ether and treated with ethanolic hydrogen chloride to give 1-(β-vinyloxyethyl)-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one hydrochloride, m.p. 213° - 215° C (dec). Recrystallization from isopropanolchloroform gives colorless prisms, m.p. 216° - 218° C (dec.).

Workup

  1. temperatureunder cooling
  2. customto stand at room temperature with occasional stirring
  3. extractionextracted with methylene chloride
  4. dry with materialdried over sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. dissolutionThe residue is dissolved in ether
  7. additiontreated with ethanolic hydrogen chloride

Sources & evidence

ORD record
ord-1f46a09e5dfa4853b659f8495b471276
Source dataset
uspto-grants-1976_11
Patent number
US03989829

Reaction notes

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