Aminoacetaldehyde dimethyl acetal → HCID 178495895, compound

HRID 972093Notes

Reaction equation

HRID 972093 reaction equation
Cl[C:2]1[CH:3]=[CH:4][C:5]2[N:11]=[C:10](SC)[N:9](C)[N:8]=[C:7](C3C=CC=CC=3)[C:6]=2[CH:21]=1.[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25][NH2:26]>C(OCCO)C>[CH3:22][O:23][CH:24]([O:27][CH3:28])[CH2:25][NH:26][C:10]1[NH:11][C:5]2[CH:4]=[CH:3][CH:2]=[CH:21][C:6]=2[CH:7]=[N:8][N:9]=1

Participants

4

Reactant 2

HCID 89728Aminoacetaldehyde dimethyl acetalHCID 6287943H-1,3,4-Benzotriazepine, 7-chloro-3-methyl-2-(methylthio)-5-phenyl-

Product 1

HCID 178495895HCID 178495895, compound

Reagents, catalysts & solvents 1

HCID 8076Glycol monoethyl etherSolvent

Procedure

A mixture of 2.66 grams (8.42 m moles) of 7-chloro-3-methyl-2-(methylthio)-5-phenyl-3H-1,3,4-benzotriazepine, 1.0 grams (9.32 m moles) of aminoacetaldehyde dimethyl acetal (98%), and 10 ml of 2-ethoxyethanol was stirred and refluxed under nitrogen for about 18 hours. The solvent was removed in vacuo on a rotary evaporator, and the residue was dissolved in diethyl ether. The resulting solution was washed in water, dried with magnesium sulfate and concentrated in vacuo. The dark residue was found to be a mixture and was chromatographed on a column containing 170 grams of alumina. The column was washed with benzene. The desired dimethoxyethylamino-1,3,4-benzotriazepine intermediate was obtained on elution with successive portions of methylene chloride and chloroform. The reactions were combined and evaporated to yield a red viscous oil.

Workup

  1. temperaturerefluxed under nitrogen for about 18 hours
  2. customThe solvent was removed in vacuo on a rotary evaporator
  3. dissolutionthe residue was dissolved in diethyl ether
  4. washThe resulting solution was washed in water
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated in vacuo
  7. customwas chromatographed on a column
  8. additioncontaining 170 grams of alumina
  9. washThe column was washed with benzene

Sources & evidence

ORD record
ord-13326c8418004a71905cfbedfb9378e7
Source dataset
uspto-grants-1979_07
Patent number
US04163104

Reaction notes

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