Hydrochloric Acid → HCID 53683030, compound

HRID 328391Notes

Reaction equation

HRID 328391 reaction equation
[Na].[C:2]([O:12][CH2:13][CH3:14])(=[O:11])[CH2:3][C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=O.Cl.[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[N:26]=[C:25]([NH:27][NH2:28])[CH2:24][N:23]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:21]=2[CH:35]=1>>[Cl:16][C:17]1[CH:18]=[CH:19][C:20]2[N:26]=[C:25]([NH:27][N:28]=[C:4]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH2:3][C:2]([O:12][CH2:13][CH3:14])=[O:11])[CH2:24][N:23]=[C:22]([C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)[C:21]=2[CH:35]=1

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 123908747-Chloro-2-hydrazinyl-5-phenyl-3H-1,4-benzodiazepineHCID 57351814Diethyl 2-oxosuccinate,sodium salt

Product 1

HCID 53683030HCID 53683030, compound

Procedure

An aqueous solution of 1.26 g. (0.006 mole) of diethyl oxalacetate sodium salt was acidified with hydrochloric acid and extracted with methylene chloride. The extract was dried over sodium sulfate and evaporated to dryness in vacuo. The resulting oil in 30 ml. of methanol under N2 was mixed with 0.812 g. (0.003 mole) of 7-chloro-2-hydrazino-5-phenyl-3H-1,4-benzodiazepine and allowed to stand at room temperature for 1.5 hours. The solution was evaporated in vacuo, dissolved in methylene chloride, washed with dilute sodium hydroxide and dried over magnesium sulfate. After filtration the solution was evaporated in vacuo giving 7-chloro-2-[[1,2-bis-(ethoxycarbonyl)ethylidene]hydrazino]-5-phenyl-3H-1,4-benzodiazepine as an oil. Nmr confirmed the structure. Nmr (CDCl3) δ 1.20 and 1.22 (2 t's, 6, CH2CH3), 4.13 (q, 6, CH2CH3), 4.48 (broad s, 2, 3--CH2), between 6.93 and 7.83 (m's, 8, arom H's).

Workup

  1. extractionextracted with methylene chloride
  2. dry with materialThe extract was dried over sodium sulfate
  3. customevaporated to dryness in vacuo
  4. additionof methanol under N2 was mixed with 0.812 g
  5. customThe solution was evaporated in vacuo
  6. dissolutiondissolved in methylene chloride
  7. washwashed with dilute sodium hydroxide
  8. dry with materialdried over magnesium sulfate
  9. filtrationAfter filtration the solution
  10. customwas evaporated in vacuo

Sources & evidence

ORD record
ord-2710c7f1f87f456d80e9b22ba705e9f8
Source dataset
uspto-grants-1977_04
Patent number
US04017492

Reaction notes

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