Acetic Acid → HCID 19770728, compound

HRID 1589785Notes

Reaction equation

HRID 1589785 reaction equation
[CH2:1]([O:8][CH2:9][C:10](Cl)=O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N([CH2:18][CH3:19])CC)C.[NH4+].[N+:21]([CH2:24][C:25]([NH-:27])=[O:26])([O-:23])=[O:22].[C:28](O)(=O)[CH3:29]>O1CCCC1.C(Cl)(Cl)Cl>[N+:21]([C:24]1[C:25](=[O:26])[NH:27][C:10]([CH2:9][O:8][CH2:1][C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=2)=[C:28]([CH2:18][CH3:19])[CH:29]=1)([O-:23])=[O:22]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 8471TriethylamineHCID 177085Benzyloxyacetyl chlorideHCID 178514238HCID 178514238, compound

Product 1

HCID 19770728HCID 19770728, compoundYield 31%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
70 °C

Procedure

Benzyloxy acetyl chloride (14.2 mL, 0.09 mol) in dry tetrahydrofuran (10 mL) was added dropwise to a solution of 1-(N-morpholino)-1-butene (12.8 g, 0.09 mol) and triethylamine (12.6 mL, 0.09 mol) in dry tetrahydrofuran (120 mL) warmed at 70° C. under a nitrogen atmosphere. After 1.25 hours, the reaction was cooled to room temperature and nitro acetamide ammonium salt (12.0 g, 0.099 mol) was added, followed by the dropwise addition of acetic acid (11.4 mL, 0.20 mol). After stirring for 20-24 hours, the reaction was diluted with chloroform (150 mL) and the solution washed with water, 10% HCl, dried (Na2SO4) and filtered through a pad of charcoal. The solvent was removed and the residue triturated with cold methanol. The crystalline yellow product was filtered, rinsed with methanol and diethyl ether to give 8.01 g (31% yield), mp 157°-158° C.

Workup

  1. temperaturethe reaction was cooled to room temperature
  2. washthe solution washed with water, 10% HCl
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered through a pad of charcoal
  5. customThe solvent was removed
  6. customthe residue triturated with cold methanol
  7. filtrationThe crystalline yellow product was filtered
  8. washrinsed with methanol and diethyl ether
  9. customto give 8.01 g (31% yield), mp 157°-158° C.

Sources & evidence

ORD record
ord-9b7e0a707ac246bb958c395f72188e02
Source dataset
uspto-grants-1993_04
Patent number
US05200329

Reaction notes

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