Acetylethanolamine → HCID 59713038, compound

HRID 2222760Notes

Reaction equation

HRID 2222760 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:23]=[CH:22][C:6]([O:7][CH:8]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:21])([F:20])[F:19])[CH:13]=2)[C:9]([OH:11])=[O:10])=[CH:5][CH:4]=1.S(Cl)(Cl)=O.[C:30]([NH:33][CH2:34][CH2:35]O)(=[O:32])[CH3:31]>ClCCCl.C1COCC1>[C:30]([NH:33][CH2:34][CH2:35][O:10][C:9](=[O:11])[CH:8]([O:7][C:6]1[CH:5]=[CH:4][C:3]([C:2]([F:24])([F:25])[F:1])=[CH:23][CH:22]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([C:18]([F:19])([F:20])[F:21])[CH:13]=1)(=[O:32])[CH3:31]

Participants

6

Reactant 3

HCID 8880AcetylethanolamineHCID 24386Thionyl ChlorideHCID 11210718HCID 11210718, compound

Product 1

HCID 59713038HCID 59713038, compoundYield 71.4%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a slurry of acid 39 (25.8 g, 0.071 mol) in anhydrous 1,2-dichloroethane (380 mL) was added thionyl chloride (16.0 mL, 0.21 mol), and then the resulting mixture was refluxed for 2 h. The mixture was cooled to rt, diluted with dry THF (150 mL) until the cloudy mixture turned clear, and then N-acetylethanolamine (39.12 g, 0.38 mol) was added. The resulting solution was stirred at rt overnight. The reaction was quenched with sat. NaHCO3 carefully, diluted with EtOAc, and washed with water. The organic layer was washed with brine, dried over Na2SO4, concentrated in vacuo, and the residue was recrystallized from iPrOH/hexanes (11 mL/31.5 mL) to afford pure product 136 (22.78 g, 71%) as a off-white solid. 1H NMR (400 MHz, CDCl3): δ 7.89 (1H, s), 7.80 (1H, d), 7.69 (1H, d), 7.57-7.61 (3H, t), 7.06 (2H, t), 5.78 (1H, s), 5.27 (1H, br), 4.24 (2H, m), 3.45 (2H, dd), 1.81 (3H, s) ppm.

Workup

  1. temperaturethe resulting mixture was refluxed for 2 h
  2. customThe reaction was quenched with sat. NaHCO3 carefully
  3. additiondiluted with EtOAc
  4. washwashed with water
  5. washThe organic layer was washed with brine
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated in vacuo
  8. customthe residue was recrystallized from iPrOH/hexanes (11 mL/31.5 mL)

Sources & evidence

ORD record
ord-7a31af6987d24a32a620d9f1ad52337c
Source dataset
uspto-grants-2008_05
Patent number
US07371888B2

Reaction notes

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