Tetrahydrofuran → HCID 19707992, compound

HRID 259660Notes

Reaction equation

HRID 259660 reaction equation
[OH:1][CH2:2][CH2:3][N:4]([CH3:20])[C:5](=[O:19])[C:6]1[C:7](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:8]([N:10]([CH2:12][CH2:13][OH:14])[CH3:11])=[O:9].C(N(CC)CC)C.[O:28]1[CH2:32][CH2:31][CH2:30]C1.[C:33](Cl)(=[O:36])[CH:34]=[CH2:35]>C(Cl)(Cl)Cl.C1C2NC3C(=CC=CC=3)SC=2C=CC=1>[C:33]([O:1][CH2:2][CH2:3][N:4]([CH3:20])[C:5](=[O:19])[C:6]1[C:7](=[CH:15][CH:16]=[CH:17][CH:18]=1)[C:8]([N:10]([CH2:12][CH2:13][O:14][C:32](=[O:28])[CH:31]=[CH2:30])[CH3:11])=[O:9])(=[O:36])[CH:34]=[CH2:35]

Participants

7

Reactant 4

HCID 8028TetrahydrofuranHCID 8471TriethylamineHCID 13140Acryloyl chlorideHCID 54303134HCID 54303134, compound

Product 1

HCID 19707992HCID 19707992, compoundYield 43%

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 N,N'-di(hydroxyethyl)-N,N'-dimethyl phthalamide (0.36 mol.), 67.8 g of triethylamine (0.72 mol.), 500 ml of tetrahydrofuran and 2 g of phenothiazine. Next, 68 g of acryloyl chloride (0.75 mol.) was slowly added to the flask over one hour. The reaction was stirred for an additional hour. The triethylamine hydrochloride salt was removed by filtration and the remaining mother liquor was evaporated with a rotoevaporator to yield a light brown liquid. The liquid was dissolved in chloroform and washed with NaCl(aq.), NH4OH(10%), NaCl(aq.) and dried over MgSO4. The chloroform was removed with a rotoevaporator to yield 60 g (43%) of a light brown liquid. The product was confirmed by IR and 13C NMR.

Workup

  1. customA one liter, three necked flask was equipped with overhead stirrer
  2. customThe triethylamine hydrochloride salt was removed by filtration
  3. customthe remaining mother liquor was evaporated with a rotoevaporator
  4. customto yield a light brown liquid
  5. washwashed with NaCl(aq.), NH4OH(10%), NaCl(aq.)
  6. dry with materialdried over MgSO4
  7. customThe chloroform was removed with a rotoevaporator

Sources & evidence

ORD record
ord-134654f87cfb45379ed2c15d3cca4cdf
Source dataset
uspto-grants-1996_06
Patent number
US05523152

Reaction notes

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