Hydrochloric Acid → HCID 12862634, compound

HRID 1395519Notes

Reaction equation

HRID 1395519 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH2:5].Cl.[CH:11]12[O:16][CH:12]1[CH2:13][CH2:14][CH2:15]2>>[ClH:1].[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][C:8]=1[Cl:9])[NH:5][C@@H:11]1[CH2:15][CH2:14][CH2:13][C@H:12]1[OH:16]

Participants

4

Reactant 3

HCID 313Hydrochloric AcidHCID 72573,4-DichloroanilineHCID 92446-Oxabicyclo[3.1.0]hexane

Product 1

HCID 12862634HCID 12862634, compoundYield 49%

Procedure

A solution of 3,4-dichloroaniline (200 g., 1.23 mole), cyclopentene oxide (400 ml.), and concentrated HCl (2 ml.) is heated at reflux temperature for seven (7) days. The unreacted epoxide is evaporated at 60° C. and the residue is treated with excess ethereal HCl, and a syrup results. This is washed with 1000 ml. of ether. The residue is crystallized and recrystallized from methanol/ether (1/5.5, v/v) to give 170.0 g. (49% yield) of trans-3,4-dichloro-N-(2-hydroxycyclopentyl)aniline, hydrochloride salt.

Workup

  1. customThe unreacted epoxide is evaporated at 60° C.
  2. additionthe residue is treated with excess ethereal HCl
  3. customa syrup results
  4. washThis is washed with 1000 ml
  5. customThe residue is crystallized
  6. customrecrystallized from methanol/ether (1/5.5
  7. customv/v) to give 170.0 g

Sources & evidence

ORD record
ord-c90b17bbbc134e8d9e7a19a10f6f750f
Source dataset
uspto-grants-1980_05
Patent number
US04204003

Reaction notes

Loading…