Ammonia → HCID 19609089, compound

HRID 1603245Notes

Reaction equation

HRID 1603245 reaction equation
Br[CH2:2][C:3]([N:5]=[C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]1[CH:12]=[CH:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:4].[NH3:20].[I-].[Na+].C(Cl)(Cl)[Cl:24]>CO.Cl>[ClH:24].[NH2:20][CH2:2][C:3]([N:5]1[C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=2[CH:13]=[CH:12][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]1=2)=[O:4]

Participants

7

Reactant 4

HCID 222AmmoniaHCID 5238Sodium IodideHCID 6212ChloroformHCID 67580135HCID 67580135, compound

Product 1

HCID 19609089HCID 19609089, compoundYield 90%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidSolventHCID 887MethanolSolvent

Conditions

Temperature
-33 °C

Procedure

A solution of 2.2 g (7 mmol) of crude N-bromoacetyl-iminostilbene (38) in 25 mL of chloroform was added carefully to 250 mL of condensed liquid ammonia at -33° C. To the reaction mixture 6.0 g (40 mmol) of sodium iodide was added, the mixture was stirred at -33° C. for 2 hours and evaporated overnight. A water-white oily solution remained and 50 mL of water was added. The solution was extracted with 2×150 mL of chloroform. The solvent was dried over Na2SO4 and evaporated to yield a clear oil that was dissolved in 25 mL of methanol saturated with hydrochloric acid (g). The resulting solution was concentrated and 25 mL of acetonitrile was added. The solid material precipitated was collected and washed with 10 mL of acetonitrile. Recrystallization in methanol/ether gave 1.8 g (6.2 mmol, 90%) of 5-(aminoacetyl)-5H-dibenzo[b,f]azepinehydrochloride (39). NMR, IR and MS data confirmed compound identity.

Workup

  1. customevaporated overnight
  2. addition50 mL of water was added
  3. extractionThe solution was extracted with 2×150 mL of chloroform
  4. dry with materialThe solvent was dried over Na2SO4
  5. customevaporated
  6. customto yield a clear oil that
  7. concentrationThe resulting solution was concentrated
  8. addition25 mL of acetonitrile was added
  9. customThe solid material precipitated
  10. customwas collected
  11. washwashed with 10 mL of acetonitrile
  12. customRecrystallization in methanol/ether

Sources & evidence

ORD record
ord-ac49f3a644cf4418875fee0ba6c875a6
Source dataset
uspto-grants-1999_11
Patent number
US05986094

Reaction notes

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