Epichlorohydrin → HCID 13371497, compound

HRID 979667Notes

Reaction equation

HRID 979667 reaction equation
[C:1]([C:6]1[CH:11]=[C:10]([NH:12][C:13]([C:15]2[S:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[O:14])[CH:9]=[CH:8][C:7]=1[OH:21])([O:3][CH2:4][CH3:5])=[O:2].[CH2:22]([CH:24]1[O:26][CH2:25]1)Cl>[Cl-].C([N+](C)(C)C)C1C=CC=CC=1.O>[C:1]([C:6]1[CH:11]=[C:10]([NH:12][C:13]([C:15]2[S:16][C:17]([CH3:20])=[CH:18][CH:19]=2)=[O:14])[CH:9]=[CH:8][C:7]=1[O:21][CH2:22][CH:24]1[O:26][CH2:25]1)([O:3][CH2:4][CH3:5])=[O:2]

Participants

5

Reactant 2

HCID 7835EpichlorohydrinHCID 13371496HCID 13371496, compound

Product 1

HCID 13371497HCID 13371497, compound

Reagents, catalysts & solvents 2

HCID 5963Benzyltrimethylammonium chlorideCatalystHCID 962WaterSolvent

Conditions

Temperature
110 °C

Procedure

In a flask, the mixture of 35 g of 2-carbethoxy 4-(5-methyl-2-thiophene carboxamido)phenol and 175 ml of epichlorohydrin, is heated to 110° C., then 2.9 g of benzyltrimethylammonium chloride are introduced. The reaction mixture is then heated to reflux for 30 mins., then cooled. Once the temperature of the medium has dropped again to 50° C., 200 ml of water are added and the mixture is stirred strongly. After decantation, the aqueous phase is extracted twice with ether and the organic phases are dried over magnesium sulfate, filtered and concentrated in vacuo. The residue hardens in ether. After three washings in 50 ml of isopropylic ether, 30 g of 1-[2-carbethoxy 4-(5-methyl 2-thiophene carboxamido)phenoxy]2,3-epoxy propane are obtained in the form of white crystals melting at 109° C.

Workup

  1. temperatureThe reaction mixture is then heated
  2. temperatureto reflux for 30 mins
  3. temperature, then cooled
  4. additionOnce the temperature of the medium has dropped again to 50° C.
  5. extractionAfter decantation, the aqueous phase is extracted twice with ether
  6. dry with materialthe organic phases are dried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0368a86019174ec9a71068aa1c545ff5
Source dataset
uspto-grants-1987_05
Patent number
US04668801

Reaction notes

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