Sodium amide → 1,5-Dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

HRID 1390377

Reaction equation

HRID 1390377 reaction equation
[NH2-].[Na+].[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[NH:8][C:7](=[O:15])[CH2:6][C:5]1=[O:16].[CH3:17]OS([O-])(=O)=O>C1(C)C(C)=CC=CC=1>[CH3:3][N:4]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]([CH3:17])[C:7](=[O:15])[CH2:6][C:5]1=[O:16]

Participants

5

Reactant 3

HCID 24533Sodium amideHCID 4694097Methyl sulfate(1-)HCID 227492411-methyl 1,2,4,5-tetrahydro 2,4-diketo 3H-1,5-benzodiazepine

Product 1

HCID 5360091,5-Dimethyl-1H-1,5-benzodiazepine-2,4(3H,5H)-dione

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2 g of sodium amide are added to a suspension of 9.5 g of 1-methyl 1,2,4,5-tetrahydro 2,4-diketo 3H-1,5-benzodiazepine, obtained in the example XIV, in 30 c.c. of xylene, and the whole is heated for about thirty minutes, while agitating, treated with 20 c.c. of methyl-sulfate and as soon as the exothermic reaction has ceased, this is heated and boiled for three hours. The solvent is evaporated under reduced presure, the residue is taken up in 200 c.c. of a 10% solution of caustic soda, and after agitation, suction filtered, and purified upon crystallisation in 90% ethanol. Yield 4.5 g; melting point: 240°-242° C.

Workup

  1. customobtained in the example XIV, in 30 c.c
  2. additiontreated with 20 c.c
  3. temperaturethis is heated
  4. customThe solvent is evaporated under reduced presure
  5. filtrationof a 10% solution of caustic soda, and after agitation, suction filtered
  6. custompurified upon crystallisation in 90% ethanol

Sources & evidence

ORD record
ord-a428d5a73b114d11858602c68098d1fb
Source dataset
uspto-grants-1979_02
Patent number
US04138572

Linked notes

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