Hydrazinecarboxylic acid, ethyl ester → HCID 21525513, compound

HRID 1658779Notes

Reaction equation

HRID 1658779 reaction equation
[CH3:1][N:2]([CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[NH:11][C:10](=S)[C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6])[CH3:3].[C:23](OCC)(=[O:26])[NH:24][NH2:25]>>[CH3:1][N:2]([CH2:4][C:5]([N:7]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[N:11]2[C:23](=[O:26])[NH:24][N:25]=[C:10]2[C:9]2[CH:19]=[CH:20][CH:21]=[N:22][C:8]1=2)=[O:6])[CH3:3]

Participants

3

Reactant 2

HCID 20064Hydrazinecarboxylic acid, ethyl esterHCID 21525533HCID 21525533, compound

Product 1

HCID 21525513HCID 21525513, compound

Procedure

A mixture of 6,11-dihydro-11-[(dimethylamino)acetyl]-5H-pyrido[2,3-b][1,5]benzodiazepin-5-thione (0.12 mole) and ethyl carbazate (1.2 mole) is heated in an oil bath preheated to 195°-205° C. using a take-off condenser (45 ml. is removed). The resulting solid is mixed with methylene chloride-water and the suspension is filtered. The filtrate is separated into layers, and the organic layer is washed with water, then brine solution and dried over anhydrous magnesium sulfate. The solvent is then evaporated and the resulting residue is repeatedly crystallized from methylene chloride to give 2,9-dihydro-9-[(dimethyl-amino)acetyl]-3H-pyrido[3,2-c]-s-triazolo[4,3-a][1,5]-benzodiazepin-3-one.

Workup

  1. temperatureis heated in an oil bath
  2. custompreheated to 195°-205° C.
  3. custom(45 ml. is removed)
  4. additionThe resulting solid is mixed with methylene chloride-water
  5. filtrationthe suspension is filtered
  6. customThe filtrate is separated into layers
  7. washthe organic layer is washed with water
  8. dry with materialbrine solution and dried over anhydrous magnesium sulfate
  9. customThe solvent is then evaporated
  10. customthe resulting residue is repeatedly crystallized from methylene chloride

Sources & evidence

ORD record
ord-1d1f851fedb94a9d8f9cce8210bcad76
Source dataset
uspto-grants-1976_06
Patent number
US03966736

Reaction notes

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