Dimethyl Sulfoxide → HCID 20361735, compound

HRID 1679777Notes

Reaction equation

HRID 1679777 reaction equation
[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[CH:7]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CS(C)=[O:22]>>[CH3:1][N:2]1[CH2:6][CH2:5][N:4]=[C:3]1[C:7]([OH:22])([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

3

Reactant 2

HCID 679Dimethyl SulfoxideHCID 54023551HCID 54023551, compound

Product 1

HCID 20361735HCID 20361735, compound

Procedure

Add 5 g. of 1-methyl-2-(2-pyridylbenzyl)imidazoline and 25 ml. of dimethyl sulfoxide to a solution of potassium t-butylate (prepared from 1.4 g. of potassium and 200 ml. of t-butanol) and stir the resulting solution in a stream of dry air for 30 hrs. Add 2.1 ml. of acetic acid to the resulting mixture and remove the alcohol in vacuo. Shake the residue with 200 ml. of benzene and 50 ml. of cooled 5 sodium carbonate. Separate the benzene phase, water-wash, dry, filter and evaporate in vacuo. Recrystallize the residue from isopropanol acetate to yield 1-methyl-2[α(-2-pyridyl) hydroxybenzyl]imidazoline, m.p. 105°-108° C.

Workup

  1. additionAdd 5 g
  2. additionAdd 2.1 ml
  3. customof acetic acid to the resulting mixture and remove the alcohol in vacuo
  4. temperatureof cooled 5 sodium carbonate
  5. customSeparate the benzene phase, water-
  6. washwash
  7. customdry
  8. filtrationfilter
  9. customevaporate in vacuo
  10. customRecrystallize the residue from isopropanol acetate

Sources & evidence

ORD record
ord-585d20d3137340fb868d7193bc08bf70
Source dataset
uspto-grants-1978_03
Patent number
US04081544

Reaction notes

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