Aminoacetaldehyde dimethyl acetal → HCID 178495884, compound

HRID 1085135Notes

Reaction equation

HRID 1085135 reaction equation
[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[NH:6][C:7](=S)[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1.[CH3:31][O:32][CH:33]([O:36][CH3:37])[CH2:34][NH2:35]>C(O)CCC.CO.CCCCC>[Cl:1][C:2]1[C:29]([Cl:30])=[CH:28][C:5]2[N:6]=[C:7]([NH:35][CH2:34][CH:33]([O:36][CH3:37])[O:32][CH3:31])[CH2:8][C:9]([C:11]3[CH:16]=[CH:15][C:14]([N:17]4[C:25]5[CH:24]=[CH:23][N:22]=[CH:21][C:20]=5[N:19]=[C:18]4[CH3:26])=[CH:13][CH:12]=3)=[N:10][C:4]=2[CH:3]=1

Participants

6

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 10479006HCID 10479006, compound

Product 1

HCID 178495884HCID 178495884, compound

Reagents, catalysts & solvents 3

HCID 2631-ButanolSolventHCID 887MethanolSolventHCID 8003PentaneSolvent

Procedure

A mixture 7,8-dichloro-2,3-dihydro-4-[4-(2-methylimidazo[4,5-c]pyrid-1-yl)phenyl]-1H-[1,5]benzodiazepin-2-thione (1.36 g, 3.0 mmol), aminoacetaldehyde dimethyl acetal (630 mg, 6.0 mmol) and red mercuric oxide (650 mg, 3.0 mmol) in n-butanol (15 ml) was heated at reflux for 2.5 hours. The mixture was cooled, diluted with methanol (50 ml) and filtered through Hyflo filter aid. The solvents were removed under reduced pressure to give a foam, which was suspended in pentane and sonicated for 5 minutes. The pentane was removed in vacuo to give the title compound, 1.10 g (70%).

Workup

  1. temperatureat reflux for 2.5 hours
  2. temperatureThe mixture was cooled
  3. filtrationfiltered through Hyflo
  4. filtrationfilter aid
  5. customThe solvents were removed under reduced pressure
  6. customto give a foam, which
  7. customsonicated for 5 minutes
  8. customThe pentane was removed in vacuo

Sources & evidence

ORD record
ord-be9725de43b7491c9cb5aa49cbb34141
Source dataset
uspto-grants-1991_04
Patent number
US05008263

Reaction notes

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