Potassium Hydroxide → HCID 3054334, compound

HRID 426588Notes

Reaction equation

HRID 426588 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[CH:13][C:14]#[N:15])[CH2:9][N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:6]=2[CH:22]=1.[OH-:23].[K+]>S(=O)(=O)(O)O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[CH:13][C:14](=[O:23])[NH2:15])[CH2:9][N:8]=[C:7]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)[C:6]=2[CH:22]=1

Participants

4

Reactant 2

HCID 14797Potassium HydroxideHCID 54463508HCID 54463508, compound

Product 1

HCID 3054334HCID 3054334, compound

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent2×

Conditions

Temperature
50 °C

Procedure

15.2 g of the 7-chloro-1-methyl-2-cyanomethylene-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine obtained in Example 1 A are subsequently portion-wise introduced into 80 ml of concentrated sulfuric acid under stirring, and the resulting suspension is slowly heated up to a temperature of 50° C. until a clear solution is formed. Subsequently, the solution is maintained at a temperature of 50° C. for 1 hour. After cooling, the solution is worked-up by pouring it on ice, neutralizing the sulfuric acid with diluted potassium hydroxide solution and extracting the raw product with methylenechloride. The organic phase is separated, washed with water until neutral reaction of the washing-water, and dried over sodium sulfate. After filtration and evaporation of the solvent a residue is obtained which is re-crystallized from ethanol. 11 g of 7-chloro-1-methyl-2-carbamoylmethylene-5-phenyl-1,3-dihydro-2H-1,4-benzodiazepine, having a melting point of 179° to 181° C., are obtained.

Workup

  1. customis formed
  2. temperatureSubsequently, the solution is maintained at a temperature of 50° C. for 1 hour
  3. temperatureAfter cooling
  4. additionby pouring it on ice
  5. extractionextracting the raw product with methylenechloride
  6. customThe organic phase is separated
  7. washwashed with water until neutral reaction of the washing-water
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration and evaporation of the solvent a residue
  10. customis obtained which
  11. customis re-crystallized from ethanol
  12. customare obtained

Sources & evidence

ORD record
ord-45b8ffe161da4702b87598ac05686f8c
Source dataset
uspto-grants-1979_10
Patent number
US04170649

Reaction notes

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