Hydrochloric Acid → HCID 178525865, compound

HRID 2163507Notes

Reaction equation

HRID 2163507 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 magneesium 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 magneesium 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-c562d875db9b4f7eb0600cc17e64efe0
Source dataset
uspto-grants-1979_01
Patent number
US04134976

Reaction notes

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