Sulfuric Acid → HCID 9949425, compound

HRID 2307344Notes

Reaction equation

HRID 2307344 reaction equation
[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:24]=[CH:23][C:20]([C:21]#[N:22])=[CH:19][CH:18]=3)=[O:16])[CH2:6][C:5]=12.S(=O)(=O)(O)[OH:26].[OH-].[NH4+]>>[CH:1]1[CH:2]=[CH:3][N:4]2[CH2:10][C:9]3[CH:11]=[CH:12][CH:13]=[CH:14][C:8]=3[N:7]([C:15]([C:17]3[CH:18]=[CH:19][C:20]([C:21]([NH2:22])=[O:26])=[CH:23][CH:24]=3)=[O:16])[CH2:6][C:5]=12

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14923Ammonium HydroxideHCID 9926821HCID 9926821, compound

Product 1

HCID 9949425HCID 9949425, compound

Procedure

4-(5H,11H-Pyrrolo[2,1-c][1,4]benzodiazepine-10-carbonyl)-benzonitrile (0.5 g) from Example 44 was added to concentrated sulfuric acid (5 ml) and the mixture was stirred for 18 hours at room temperature to yield a bright yellow solution. The solution was poured onto ice and made basic with the addition of concentrated ammonium hydroxide. The resultant solid was filtered, dissolved in dichloromethane, and filtered through a short column of hydrous sodium magnesium silicate and further eluted with several volumes of dichloromethane. The combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization occurred. After cooling, the crystals were collected by filtration to yield the title compound (5.05 g), m.p. 226-228° C.

Workup

  1. customto yield a bright yellow solution
  2. additionThe solution was poured onto ice
  3. filtrationThe resultant solid was filtered
  4. dissolutiondissolved in dichloromethane
  5. filtrationfiltered through a short column of hydrous sodium magnesium silicate
  6. washfurther eluted with several volumes of dichloromethane
  7. concentrationThe combined organic phase was concentrated on a hot plate with the gradual addition of hexane until crystallization
  8. temperatureAfter cooling
  9. filtrationthe crystals were collected by filtration

Sources & evidence

ORD record
ord-bf87809f72e84c9389cb2e5ab9cb9140
Source dataset
uspto-grants-2004_12
Patent number
US06831079B1

Reaction notes

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