Cyanoacetic acid hydrazide → HCID 12562505, compound

HRID 597070

Reaction equation

HRID 597070 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.[C:20]([CH2:22][C:23]([NH:25][NH2:26])=O)#[N:21]>C(O)CCC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:23]([CH2:22][C:20]#[N:21])=[N:25][N:26]=[C:10]3[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

Participants

4

Reactant 2

HCID 8820Cyanoacetic acid hydrazideHCID 826706Thionordiazepam

Product 1

HCID 12562505HCID 12562505, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A mixture of 1,3-dihydro-7-chloro-5-phenyl-2H-1,4-benzodiazepine-2-thione (5.72 g., 0.02 mole), cyanoacetic acid hydrazide (5.95 g., 0.06 mole) and n-butylalcohol (275 ml.) is refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture. The mixture is then concentrated in vacuo. The resulting residue is suspended in water and extracted with methylene chloride. The extract was dried and concentrated. The residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3. The product eluted from the column is crystallized from ethyl acetate-Skellysolve B hexanes to give 2.62 g. of 8-chloro-6-phenyl-4H-s-triazolo[4,3a][1,4]benzodiazepine-1-acetonitrile of melting point 198°-201° C.

Workup

  1. temperatureis refluxed for 7.5 hours with a slow stream of nitrogen bubbling through the mixture
  2. concentrationThe mixture is then concentrated in vacuo
  3. extractionextracted with methylene chloride
  4. customThe extract was dried
  5. concentrationconcentrated
  6. customThe residue is chromatographed on silica gel (400 g.) with 2% methanol- 98% CHCl3
  7. washThe product eluted from the column
  8. customis crystallized from ethyl acetate-Skellysolve B hexanes
  9. customto give 2.62 g

Sources & evidence

ORD record
ord-fdd650ad424349b2a7679bb70ae0f147
Source dataset
uspto-grants-1977_03
Patent number
US04012413

Linked notes

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