Hydrochloric Acid → HCID 20392259, compound

HRID 1863159Notes

Reaction equation

HRID 1863159 reaction equation
[CH:1]1([C:4]([N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][C:9](=O)[C:8]3=[CH:18][S:19][CH:20]=[C:7]23)=[O:5])[CH2:3][CH2:2]1.B.[ClH:22].C(O)C>O1CCCC1>[ClH:22].[CH:1]1([C:4]([N:6]2[C:12]3[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=3[NH:10][CH2:9][C:8]3=[CH:18][S:19][CH:20]=[C:7]23)=[O:5])[CH2:2][CH2:3]1

Participants

6

Reactant 4

HCID 313Hydrochloric Acid2×HCID 702Ethanol2×HCID 6331BoraneHCID 20392240HCID 20392240, compound

Product 1

HCID 20392259HCID 20392259, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To 5.69 g. of 4-cyclopropylcarbonyl-4,9-dihydro-10H-thieno[3,4-b][1,5]benzodiazepin-10-one in 100 ml. of tetrahydrofuran is added 120 ml. of 1 M borane in tetrahydrofuran under argon, with stirring in an ice bath. The mixture is refluxed for 18 hours, then chilled and 60 ml. of 6 N hydrochloric acid is cautiously added. Most of the solvent is evaporated and 100 ml. of 5 N sodium hydroxide is added. The mixture is extracted with methylene chloride, dried over magnesium sulfate and evaporated giving a gum. Excess hydrochloric acid and ethanol are added to the gum and then evaporated giving a second gum. Ethanol is added to this second gum producing crystals which are recovered giving the desired product as colorless crystals, mp. 157°-159° C. (dec.).

Workup

  1. temperatureThe mixture is refluxed for 18 hours
  2. temperaturechilled
  3. customMost of the solvent is evaporated
  4. additionof 5 N sodium hydroxide is added
  5. extractionThe mixture is extracted with methylene chloride
  6. dry with materialdried over magnesium sulfate
  7. customevaporated
  8. customgiving a gum
  9. customevaporated
  10. customgiving a second gum
  11. customproducing crystals which
  12. customare recovered

Sources & evidence

ORD record
ord-138e536e94bd43dd81869a0c7540725d
Source dataset
uspto-grants-1979_09
Patent number
US04168269

Reaction notes

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