Hydrochloric Acid → 1-Chloro-3-(2,4-dichloroanilino)propan-2-ol

HRID 2058316Notes

Reaction equation

HRID 2058316 reaction equation
[Cl:1][C:2]1[CH:8]=[C:7]([Cl:9])[CH:6]=[CH:5][C:3]=1[NH2:4].[CH2:10]([CH:12]1[O:14][CH2:13]1)[Cl:11].Cl>C(O)C>[Cl:11][CH2:10][CH:12]([OH:14])[CH2:13][NH:4][C:3]1[CH:5]=[CH:6][C:7]([Cl:9])=[CH:8][C:2]=1[Cl:1]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 7835EpichlorohydrinHCID 111232,4-Dichloroaniline

Product 1

HCID 233502121-Chloro-3-(2,4-dichloroanilino)propan-2-olYield 41.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

324.0 Grams (2.0 mol) of 2,4-dichloroaniline, 400 ml absolute ethanol, 185.1 g (2.0 mol) of epichlorohydrin and 3 g of conc. hydrochloric acid are added together in this sequence with stirring and then allowed to stand for 12 days. The solution is thereafter concentrated in vacuum to a brown oily residue which is distilled in high vacuum. The main fraction, which boils between 130° C. and 153° C./0.01 Torr, is collected and redistilled, yielding 209 g of N-(3-chloro-2-hydroxypropyl)-2,4-dichloroaniline as a clear liquid, boiling at 142°-145° C./0.01 Torr.

Workup

  1. concentrationThe solution is thereafter concentrated in vacuum to a brown oily residue which
  2. distillationis distilled in high vacuum
  3. customboils between 130° C. and 153° C.
  4. customis collected
  5. distillationredistilled

Sources & evidence

ORD record
ord-a92459d7023341b789be94c321ee677f
Source dataset
uspto-grants-1980_07
Patent number
US04215220

Reaction notes

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