Sulfuric Acid → HCID 3054335, compound

HRID 426589Notes

Reaction equation

HRID 426589 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][C:17]=3[Cl:22])[C:6]=2[CH:23]=1.S(=O)(=O)(O)[OH:25].[OH-].[Na+]>>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[CH:13][C:14](=[O:25])[NH2:15])[CH2:9][N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 14798Sodium HydroxideHCID 54563792HCID 54563792, compound

Product 1

HCID 3054335HCID 3054335, compound

Conditions

Temperature
50 °C

Procedure

5.4 g of 7-chloro-1-methyl-2-cyanomethylene-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine are introduced portion-wise into 26 ml of concentrated sulfuric acid and are dissolved therein while the mixture is slowly heated-up to a temperature of 50° C. The solution is kept at a temperature of 50° C. for 1 more hour. For working-up after cooling the solution is poured onto ice, the sulfuric acid is neutralized with diluted sodiumhydroxide solution and the raw product is extracted with methylenechloride. The organic phase is separated, washed with water to neutral reaction and dried over sodium sulfate. After filtration and evaporation of the solvent under vacuum, a residue is obtained and is crystallized by trituration with ether. After re-crystallization from ethanol, 7-chloro-1-methyl-2-carbamoylmethylene-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine, having a melting point of 212° to 217° C., is obtained.

Workup

  1. dissolutionare dissolved
  2. customis kept at a temperature of 50° C. for 1 more hour
  3. temperatureafter cooling the solution
  4. additionis poured onto ice
  5. extractionthe raw product is extracted with methylenechloride
  6. customThe organic phase is separated
  7. washwashed with water to neutral reaction
  8. dry with materialdried over sodium sulfate
  9. filtrationAfter filtration and evaporation of the solvent under vacuum
  10. customa residue is obtained
  11. customis crystallized by trituration with ether
  12. customAfter re-crystallization from ethanol, 7-chloro-1-methyl-2-carbamoylmethylene-5-(2'-chlorophenyl)-1,3-dihydro-2H-1,4-benzodiazepine
  13. customis obtained

Sources & evidence

ORD record
ord-2e287eda73c44f14898796472436fd71
Source dataset
uspto-grants-1979_10
Patent number
US04170649

Reaction notes

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