Dimethyl Sulfoxide → HCID 20361735, compound

HRID 1580310Notes

Reaction equation

HRID 1580310 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. customSeparate the benzene phase, water-
  5. washwash
  6. customdry
  7. filtrationfilter
  8. customevaporate in vacuo
  9. customRecrystallize the residue from isopropanol acetate

Sources & evidence

ORD record
ord-6fb6d1e3cb634ebcbb7f11fd90005268
Source dataset
uspto-grants-1976_01
Patent number
US03932431

Reaction notes

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