Ammonia → HCID 20363505, compound

HRID 596147Notes

Reaction equation

HRID 596147 reaction equation
[CH3:1][S:2]([CH2:5][CH2:6][NH:7][C:8]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=1[C:10]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=O)(=[O:4])=[O:3].[O:23]1[C:27](=O)[CH2:26][NH:25]C1=O.Cl.N>C(Cl)Cl>[CH3:1][S:2]([CH2:5][CH2:6][N:7]1[C:8]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:9]=2[C:10]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[N:25][CH2:26][C:27]1=[O:23])(=[O:4])=[O:3]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 75136Oxazolidine-2,5-dioneHCID 20363553HCID 20363553, compound

Product 1

HCID 20363505HCID 20363505, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 0.5 g of 2-(β-methylsulfonylethyl)amino- 5-chlorobenzophenone in 20 ml of dry methylene chloride is added 0.5 g of oxazolidine-2,5-dione. To the mixture is added 20 ml of ethereal hydrogen chloride under cooling. The mixture is stirred at room temperature. After completion of the reaction, the mixture is poured into ice water, basified with aqueous ammonia and extracted with methylene chloride. The extracts are combined and dried over anhydrous sodium sulfate, and the solvent is removed under reduced pressure. The residue is added with isopropyl alcohol to form crystals. Recrystallization from acetone gives 1-(β-methylsulfonylethyl)-5-phenyl-7-chloro-1,3-dihydro-2H-1,4-benzodiazepin-2-one as colorless leaflets, m.p. 218° - 219° C.

Workup

  1. temperatureunder cooling
  2. customAfter completion of the reaction
  3. extractionextracted with methylene chloride
  4. dry with materialdried over anhydrous sodium sulfate
  5. customthe solvent is removed under reduced pressure
  6. additionThe residue is added with isopropyl alcohol
  7. customto form crystals
  8. customRecrystallization from acetone

Sources & evidence

ORD record
ord-1ec4974d8a4f4f478ef3c9b5fc6d19b6
Source dataset
uspto-grants-1977_03
Patent number
US04010154

Reaction notes

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