Methanol → Uxepam

HRID 442328Notes

Reaction equation

HRID 442328 reaction equation
[Na].[C:2]([N:5]1[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:10]2[CH:18]=[C:19]([Cl:22])[CH:20]=[CH:21][C:9]=2[NH:8][C:7](=[O:23])[CH2:6]1)(=[O:4])[NH2:3].[CH3:24]O>>[CH3:24][N:8]1[C:9]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:10]=2[CH:11]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:5]([C:2](=[O:4])[NH2:3])[CH2:6][C:7]1=[O:23]

Participants

4

Reactant 3

HCID 887Methanol2×HCID 5360545SodiumHCID 14475297HCID 14475297, compound

Product 1

HCID 68787UxepamYield 79.5%

Procedure

0.16 g. (6.85 mmoles) of metallic sodium are dissolved in 2 ml. of absolute methanol, and a suspension of 0.9 g. (2.86 mmoles) of 4-carbamoyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one in 50 ml. of absolute methanol is added to the solution at room temperature, with stirring. The suspension is stirred at room temperature for 30 minutes, and then evaporated under reduced pressure. The oily residue is dissolved in 9 ml. of dimethyl formamide, and 0.48 ml. of methyl iodide are added to the stirred solution at room temperature. The mixture is stirred for additional 2 hours, then diluted with 50 ml. of water and extracted with 3 × 10 ml. of chloroform. The chloroform extracts are combined, dried over sodium sulfate, filtered, and the filtrate is evaporated under reduced pressure, to obtain 0.85 g. of a residue, which is recrystallized from ethanol. 0.75 g. (79.5 %) of 1-methyl-4-carbamoyl-5-phenyl-7-chloro-1,3,4,5-tetrahydro-2H-1,4-benzodiazepine-2-one are obtained; m.p.: 217°-220° C.

Workup

  1. stirringThe suspension is stirred at room temperature for 30 minutes
  2. customevaporated under reduced pressure
  3. dissolutionThe oily residue is dissolved in 9 ml
  4. additionof methyl iodide are added to the stirred solution at room temperature
  5. stirringThe mixture is stirred for additional 2 hours
  6. additiondiluted with 50 ml
  7. extractionof water and extracted with 3 × 10 ml
  8. dry with materialdried over sodium sulfate
  9. filtrationfiltered
  10. customthe filtrate is evaporated under reduced pressure
  11. customto obtain 0.85 g
  12. customof a residue, which is recrystallized from ethanol

Sources & evidence

ORD record
ord-7607a34277d340dd9a2dd8a445e465b8
Source dataset
uspto-grants-1977_08
Patent number
US04045433

Reaction notes

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