Hydrochloric Acid → HCID 70614510, compound

HRID 1112002Notes

Reaction equation

HRID 1112002 reaction equation
[CH3:1][S:2]([C:5]1[C:6](C)=[CH:7][C:8](O)=[CH:9]C=1)(=[O:4])=[O:3].[CH2:13]([CH:15]1[O:17][CH2:16]1)[Cl:14].N1CCCC1.[CH:23]([NH2:26])([CH3:25])[CH3:24].[I-].[K+].Cl.[CH2:30]([OH:32])[CH3:31]>>[ClH:14].[CH:23]([NH:26][CH2:31][CH:30]([OH:32])[CH2:16][O:17][C:15]1[CH:13]=[C:8]([CH3:9])[CH:7]=[CH:6][C:5]=1[S:2]([CH3:1])(=[O:3])=[O:4])([CH3:25])[CH3:24]

Participants

8

Reactant 7

HCID 313Hydrochloric AcidHCID 702Ethanol2×HCID 4875Potassium IodideHCID 6363IsopropylamineHCID 7835Epichlorohydrin2×HCID 31268PyrrolidineHCID 1670483-Methyl-4-(methylsulfonyl)phenol

Product 1

HCID 70614510HCID 70614510, compound

Procedure

A mixture of 4-(methylsulfonyl)-m-cresol (18.6 g., 0.1 mole), epichlorohydrin (60 g., 0.65 mole) and 0.6 g. of pyrrolidine is heated on steam bath for 12 hr. Excess epichlorohydrin is removed under reduced pressure, the resulting chlorohydrin derivative taken up in 50 ml. of absolute ethanol and filtered through diatomaceous earth. Isopropylamine (50 g., 0.85 mole) and 0.1 g. of potassium iodide are added to the ethanol filtrate of the epichlorohydrin derivative and the mixture is refluxed for 18 hr. and filtered. Concentration of the filtrate under reduced pressure affords a residue which is taken up in 70 ml. of 1N hydrochloric acid and 300 ml. of absolute ethanol. Distillables are removed under reduced pressure and the resulting residue stirred with ether to provide solid crude product. Crystallization of the crude product from butanone-methanol and again from 95% ethanol-ether, affords 1-(ISOPROPYLAMINO)-3-[4-(METHYLSULFONYL)-m-TOLYLOXY]-2-PROPANOL HYDROCHLORIDE, m.p. 177.0°-179.0° C. (corr.) in a 62% overall yield. A sample, m.p. 176.0°-178.0° C. (corr), analyzed as follows.

Workup

  1. customExcess epichlorohydrin is removed under reduced pressure
  2. filtrationof absolute ethanol and filtered through diatomaceous earth
  3. temperaturethe mixture is refluxed for 18 hr
  4. filtrationand filtered
  5. customConcentration of the filtrate under reduced pressure affords a residue which
  6. customDistillables are removed under reduced pressure
  7. customto provide solid crude product
  8. customCrystallization of the crude product from butanone-methanol

Sources & evidence

ORD record
ord-5c4277a6910149a086081de8773a7f22
Source dataset
uspto-grants-1978_10
Patent number
US04119729

Reaction notes

Loading…