Ethylene Glycol → HCID 54566081, compound

HRID 1763667Notes

Reaction equation

HRID 1763667 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[O:17])=[O:2].[CH2:18](O)[CH2:19][OH:20].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[O:2]1[CH2:18][CH2:19][O:20][CH:1]1[C:3]1[CH:4]=[C:5]2[N:11]([CH:12]=1)[CH2:10][CH2:9][C:8]1[CH:13]=[CH:14][CH:15]=[CH:16][C:7]=1[C:6]2=[O:17]

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 6101p-Toluenesulfonic acidHCID 13152886HCID 13152886, compound

Product 1

HCID 54566081HCID 54566081, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 5 gm. of 6,11-dihydro-2-formyl-5H-pyrrolo[2,1-b][3]benzazepin-11-one, 2.5 gm. of ethylene glycol, 0.5 gm. of p-toluenesulfonic acid and 100 ml. of toluene is refluxed for 16 hr. in an apparatus designed to remove water formed during the reaction (Dean-Stark apparatus). The reaction mixture is cooled to 0° C. and washed rapidly with ice cold 5% sodium carbonate solution (2 × 50 ml.) and dried over Na2SO4. Evaporation of the solvent leaves 6,11-dihydro-2-(2-dioxolanyl)-5H-pyrrolo[2,1-b][3]benzazepin-11-one as an oil which is of sufficient purity for use in the next step.

Workup

  1. additionA mixture of 5 gm
  2. customto remove water
  3. customformed during the reaction (Dean-Stark apparatus)
  4. washwashed rapidly with ice cold 5% sodium carbonate solution (2 × 50 ml.)
  5. dry with materialdried over Na2SO4
  6. customEvaporation of the solvent

Sources & evidence

ORD record
ord-9c0a6172a7434d588f2784a043e52290
Source dataset
uspto-grants-1978_09
Patent number
US04112112

Reaction notes

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