Hydrochloric Acid → HCID 20528504, compound

HRID 67088Notes

Reaction equation

HRID 67088 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]#[N:11])[CH:5]=[CH:4][C:3]=1[OH:12].C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH2:24](N)[CH2:25][NH2:26].ClC1C=CC=CC=1Cl.Cl>C(O)(C)C>[ClH:1].[Cl:1][C:2]1[CH:7]=[C:6]([S:8][CH2:9][C:10]2[NH:26][CH2:25][CH2:24][N:11]=2)[CH:5]=[CH:4][C:3]=1[OH:12]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 72391,2-DichlorobenzeneHCID 2250301,2-Ethanediamine, 4-methylbenzenesulfonate (1:?)HCID 101303832-Chloro-4-(cyanomethylthio)-phenol

Product 1

HCID 20528504HCID 20528504, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

A mixture of 19.95 g of 2-chloro-4-(cyanomethylthio)-phenol, 23.3 g of ethylenediamine p-toluenesulfonate and 75 ml of 1,2-dichlorobenzene was heated at 160°-175° C. with stirring under a small flow of nitrogen for 1.5 hours. After cooling the reaction mixture, the 1,2-dichlorobenzene was decanted off. The residue was slurried in water and CH2Cl2 and then basified. The CH2Cl2 layer was separated from the mixture and an insoluble gum obtained. The gum was put in solution in isopropyl alcohol, acidified with hydrochloric acid in isopropyl alcohol and then cooled. The crude product was removed by filtering and recrystallized from isopropyl alcohol. Recrystallized 2-chloro-4-(((2-imidazolin-2-yl)methyl)thio)-phenol hydrochloride was found to have a m.p. of 181°-183° C.

Workup

  1. temperaturewas heated at 160°-175° C.
  2. temperatureAfter cooling the reaction mixture
  3. customthe 1,2-dichlorobenzene was decanted off
  4. customThe CH2Cl2 layer was separated from the mixture
  5. customan insoluble gum obtained
  6. temperaturecooled
  7. customThe crude product was removed
  8. filtrationby filtering
  9. customrecrystallized from isopropyl alcohol

Sources & evidence

ORD record
ord-290b4ebf48a242a79f6c5ae8945b2210
Source dataset
uspto-grants-1982_08
Patent number
US04344958

Reaction notes

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