Triethylamine → HCID 53860162, compound

HRID 1079291Notes

Reaction equation

HRID 1079291 reaction equation
[OH:1][CH2:2][CH2:3][CH:4]1[N:8]([CH3:9])[CH:7]=[CH:6][S:5]1.C(N(CC)CC)C.[C:17](Cl)(=[O:20])[CH:18]=[CH2:19]>C1C2NC3C(=CC=CC=3)SC=2C=CC=1.C(Cl)(Cl)Cl>[C:17]([O:1][CH2:2][CH2:3][CH:4]1[N:8]([CH3:9])[CH:7]=[CH:6][S:5]1)(=[O:20])[CH:18]=[CH2:19]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 22910805HCID 22910805, compound

Product 1

HCID 53860162HCID 53860162, compoundYield 82%

Reagents, catalysts & solvents 2

HCID 7108PhenothiazineCatalystHCID 6212ChloroformSolvent

Procedure

A one liter, three necked flask was equipped with overhead stirrer, nitrogen atmosphere and an addition funnel. The flask was charged with 100 g of 2-(2-hydroxyethyl)-3-methylthiazole (0.70 mol.), 71 g of triethylamine (0.70 mol.), 500 g of chloroform and 3 g of phenothiazine. Next, 63 g of acryloyl chloride (0.70 mol.) was slowly added to the reaction over 1.5 hour via the addition funnel. The reaction was stirred for 2 hours at room temperature. The reaction mixture was extracted with NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was evaporated with a rotoevaporator to yield 113 g (82%) of a dark brown liquid. The compound was confirmed by IR and 13C NMR.

Workup

  1. customA one liter, three necked flask was equipped with overhead stirrer
  2. extractionThe reaction mixture was extracted with NaCl(aq.), NH4OH(10%), NaCl(aq.)
  3. dry with materialdried over MgSO4
  4. customThe chloroform was evaporated with a rotoevaporator

Sources & evidence

ORD record
ord-2e03c248c7284ef4a260aa49babf6cf9
Source dataset
uspto-grants-1996_12
Patent number
US05580647

Reaction notes

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