2-Chloroethanol → HCID 131712944, compound

HRID 1164468Notes

Reaction equation

HRID 1164468 reaction equation
[CH2:1]([Cl:4])[CH2:2][OH:3].[I-].[K+].[CH3:7][C:8]1[CH:13]=[CH:12][CH:11]=[C:10]([CH3:14])[C:9]=1[N:15]1[CH2:19][CH:18]([CH3:20])[N:17]([C:21]2[C:26]([CH3:27])=[CH:25][CH:24]=[CH:23][C:22]=2[CH3:28])[C:16]1=N.O.C[N:32](C)C=O>>[ClH:4].[CH3:14][C:10]1[CH:11]=[CH:12][CH:13]=[C:8]([CH3:7])[C:9]=1[N:15]1[C:19](=[NH:32])[CH:18]([CH3:20])[N:17]([C:21]2[C:22]([CH3:28])=[CH:23][CH:24]=[CH:25][C:26]=2[CH3:27])[CH:16]1[CH2:1][CH2:2][OH:3]

Participants

6

Reactant 5

HCID 342-ChloroethanolHCID 962WaterHCID 4875Potassium IodideHCID 6228DimethylformamideHCID 20512409HCID 20512409, compound

Product 1

HCID 131712944HCID 131712944, compoundYield 34.3%

Procedure

1.5 ml (1.8 g, 0.022 moles) of ethylene chlorohydrine and 0.35 g (0.002 moles) of potassium iodide are added to a solution of 6.14 g (0.02 moles) of 1,3-bis(2',6'-dimethylphenyl)-2-imino-4-methyl-imidazolidine, obtained as described in Example 3, in 60 ml of dry dimethylformamide. The resulting mixture is stirred at 100° to 105° C. for 6 hours, thereafter it is poured onto 300 ml of icy water. The separated product is filtered off, washed with water and ethyl acetate, and dried. 1.6 g of 1,3-bis(2',6'-dimethylphenyl)-2-(β-hydroxyethyl)-imino-4-methyl-imidazolidine hydrochloride are obtained; m.p.: 288°-291° C. (after recrystallization from a 6:4 mixture of methanol and water).

Workup

  1. customobtained
  2. filtrationThe separated product is filtered off
  3. washwashed with water and ethyl acetate
  4. customdried

Sources & evidence

ORD record
ord-09da78afeebf42a2bb0ce63d4f09e3f1
Source dataset
uspto-grants-1983_01
Patent number
US04369325

Reaction notes

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