HCID 11393673, compound → HCID 18183133, compound

HRID 430655Notes

Reaction equation

HRID 430655 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:16]3[CH:17]=[C:18]4[O:23][CH2:22][O:21][C:19]4=[CH:20][C:15]=3[CH2:14][C:13](=S)[NH:12][N:11]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].[NH2:25][CH2:26][C:27]1([CH:32]2[CH2:34][CH2:33]2)OCCO1>COCCO.[Hg]=O>[CH:32]1([C:27]2[N:12]3[N:11]=[C:10]([C:7]4[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=4)[C:16]4[CH:17]=[C:18]5[O:23][CH2:22][O:21][C:19]5=[CH:20][C:15]=4[CH2:14][C:13]3=[N:25][CH:26]=2)[CH2:34][CH2:33]1

Participants

5

Reactant 2

HCID 11393673HCID 11393673, compoundHCID 18183154HCID 18183154, compound

Product 1

HCID 18183133HCID 18183133, compound

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 80192-MethoxyethanolSolvent

Conditions

Temperature
110 °C

Procedure

A suspension of 0.50 g (1.47 mmol) of 5-(4-nitrophenyl)-8,9-dihydro-7H-1,3-dioxolo[4,5-h][2,3]benzodiazepine-8-thione (Example 15D) and 0.42 g (2.94 mmol) of 2-aminomethyl-2-cyclopropyl-1,3-dioxolane in 12 ml of Methyl Cellosolve® with 0.32 g (1.47 mmol) of red mercury oxide is stirred for 12 hours at 110° C. After filtration, the mixture is concentrated by evaporation to a volume of 5 ml and poured into water. The precipitate is suctioned off and dissolved in 10 ml of a 1:1 mixture of concentrated hydrochloric acid and glacial acetic acid and heated to boiling for 1.5 hours. During cooling, the hydrochloride salt of the title compound precipitates.

Workup

  1. filtrationAfter filtration
  2. concentrationthe mixture is concentrated by evaporation to a volume of 5 ml
  3. additionpoured into water
  4. dissolutiondissolved in 10 ml of a 1:1 mixture of concentrated hydrochloric acid and glacial acetic acid
  5. temperatureheated
  6. waitto boiling for 1.5 hours
  7. temperatureDuring cooling
  8. customthe hydrochloride salt of the title compound precipitates

Sources & evidence

ORD record
ord-643cc8ae4382498b891cd8404c7f2ef8
Source dataset
uspto-grants-2001_11
Patent number
US06323197B1

Reaction notes

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