Aminoacetaldehyde dimethyl acetal → HCID 20094057, compound

HRID 273781Notes

Reaction equation

HRID 273781 reaction equation
S=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[CH2:4][NH:3]1.[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH2:24][NH2:25]>O>[CH3:21][O:22][CH:23]([O:26][CH3:27])[CH2:24][NH:25][C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[N:6]2[CH:13]=[N:14][C:15]([C:16]([O:18][CH2:19][CH3:20])=[O:17])=[C:5]2[CH2:4][N:3]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 20093949HCID 20093949, compound

Product 1

HCID 20094057HCID 20094057, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2.1. 6.0 g of ethyl 5,6-dihydro-6-thioxo-4H-imidazo-[1,5-a][1,4]benzodiazepine-3-carboxylate in 40 ml of amino-acetaldehyde dimethyl acetal are stirred at 85° C. for 48 h. The mixture is diluted with 150 ml of water and extracted four times with ethyl acetate. The organic extracts are washed with saturated aqueous sodium chloride solution and evaporated in a vacuum. The residue is chromatographed over silica gel. Elution is carried out with dichloromethane/ethanol 99:1, 98:2 and 97:3. The crude eluate is recrystallized from ethyl acetate/diisopropyl ether. There are obtained 4.3 g of pure ethyl 6-[(2,2-dimethoxy-ethyl)amino]-4H-imidazo[1,5-a][1,4]-benzodiazepine-3-carboxylate of m.p. 121°-122° C.

Workup

  1. extractionextracted four times with ethyl acetate
  2. washThe organic extracts are washed with saturated aqueous sodium chloride solution
  3. customevaporated in a vacuum
  4. customThe residue is chromatographed over silica gel
  5. washElution
  6. customThe crude eluate is recrystallized from ethyl acetate/diisopropyl ether

Sources & evidence

ORD record
ord-37e175922841431d874dfdb363bc113e
Source dataset
uspto-grants-1995_02
Patent number
US05387585

Reaction notes

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