Hydrochloric Acid → HCID 178525865, compound

HRID 442156

Reaction equation

HRID 442156 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[NH:11][C:10](=S)[CH2:9][N:8]=[C:7]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[C:6]=2[CH:19]=1.[NH2:20][CH2:21][C:22]([OH:24])=[O:23].C(=O)([O-])[O-].[Na+].[Na+].Cl>O.C(O)C>[C:22]([CH2:21][NH:20][C:10]1[CH2:9][N:8]=[C:7]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:6]2[CH:19]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]=1)([OH:24])=[O:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 750GlycineHCID 10340Sodium CarbonateHCID 826706Thionordiazepam

Product 1

HCID 178525865HCID 178525865, compoundYield 77.5%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A suspension of 3.5 g of 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepine-2-thione, 5.5 g of glycine, 5.5 g of sodium carbonate, 100 ml of ethanol and 30 ml of water was refluxed with stirring for an hour and the mixture was poured into water. The pH of the solution was adjusted to 4 by addition of 2N hydrochloric acid and was extracted with chloroform. The mixture was filtered and the filtrate was dried over magnesium sulfate and evaporated to dryness. The gummy residue was crystallized by trituration with methanol and the mixture was filtered. The recovered solid was crystallized from ethanol to obtain 3.1 g (77% yield) of 2-carboxymethylamino-7-chloro-5-phenyl-3H-1,4-benzodiazepine melting at 215°-220° C.

Workup

  1. temperaturewas refluxed
  2. extractionwas extracted with chloroform
  3. filtrationThe mixture was filtered
  4. dry with materialthe filtrate was dried over magnesium sulfate
  5. customevaporated to dryness
  6. customThe gummy residue was crystallized by trituration with methanol
  7. filtrationthe mixture was filtered
  8. customThe recovered solid was crystallized from ethanol

Sources & evidence

ORD record
ord-81a320b18c4c4c4aa09e4fb72f69d2c3
Source dataset
uspto-grants-1977_08
Patent number
US04044142

Linked notes

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