Aminoacetaldehyde dimethyl acetal → HCID 178495877, compound

HRID 1076201Notes

Reaction equation

HRID 1076201 reaction equation
[CH:1]1[C:11]2[C:10](=S)[NH:9][C:8]3[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=3[NH:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20][NH2:21]>C(O)CCC>[CH3:17][O:18][CH:19]([O:22][CH3:23])[CH2:20][NH:21][C:10]1[C:11]2[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=2[NH:6][C:7]2[CH:16]=[CH:15][CH:14]=[CH:13][C:8]=2[N:9]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 303289111H-Dibenzo(b,e)(1,4)diazepine-11-thione, 5,10-dihydro-

Product 1

HCID 178495877HCID 178495877, compound

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

5,10-Dihydro-11H-dibenzo[b,e][1,4]diazepine-11-thione (33.75 g., 150 mmol.) is suspended in 450 ml. of n-butyl alcohol and treated with 47.25 g. (450 mmol.) of commerical aminoacetaldehyde dimethyl acetal. The reagents are heated for 5.5 hours during which time the solution turns brown. The solution is cooled to room temperature and the solvent is removed in vacuo. The residue is dissolved in 600 ml. of hot ethyl acetate, filtered, concentrated to 400 ml. and cooled to give 36.0 g. (81%) of [(5H-dibenzo[b,e][1,4]diazepin-11-yl)amio]acetaldehyde dimethyl acetal of melting point 181°-182.5° C. A second crop (2.55 g., 5.7%) of melting point 181.5°-184° C. is also collected.

Workup

  1. temperatureThe reagents are heated for 5.5 hours during which time the solution
  2. customthe solvent is removed in vacuo
  3. dissolutionThe residue is dissolved in 600 ml
  4. filtrationof hot ethyl acetate, filtered
  5. concentrationconcentrated to 400 ml
  6. temperatureand cooled
  7. customto give 36.0 g
  8. customA second crop (2.55 g., 5.7%) of melting point 181.5°-184° C. is also collected

Sources & evidence

ORD record
ord-35aa614ba965408db4fdad99db1a9d58
Source dataset
uspto-grants-1976_05
Patent number
US03956297

Reaction notes

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