Hydrochloric Acid → HCID 53702067, compound

HRID 1650709Notes

Reaction equation

HRID 1650709 reaction equation
[NH2:1][C:2]([C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1)=[C:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5].N1C=CC=CC=1.[C:22](Cl)(=[O:24])[CH3:23].Cl>O1CCCC1.O>[C:22]([NH:1][C:2]([C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=1)=[C:3]([CH3:9])[C:4]([O:6][CH2:7][CH3:8])=[O:5])(=[O:24])[CH3:23]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 6367Acetyl chlorideHCID 312935HCID 312935, compound

Product 1

HCID 53702067HCID 53702067, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

76 g of ethyl 3-amino-2-methyl-3-phenyl-2-propenoate were maintained at 15° C. in 600 ml of tetrahydrofuran and 32.3 ml of pyridine while adding 28.44 ml of acetyl chloride in 100 ml of tetrahydrofuran. The mixture was refluxed for 1 hour, then cooled and poured into a liter of water acidified to pH 1 with 2N hydrochloric acid. After extracting with ether, washing with water, with a saturated solution of sodium bicarbonate and then with water, drying and concentrating to dryness under reduced pressure, 80 g of the expected product were obtained.

Workup

  1. temperatureThe mixture was refluxed for 1 hour
  2. temperaturecooled
  3. extractionAfter extracting with ether
  4. washwashing with water, with a saturated solution of sodium bicarbonate
  5. dry with materialwith water, drying
  6. concentrationconcentrating to dryness under reduced pressure

Sources & evidence

ORD record
ord-3a0d9f2b6dcf4747a18d96f81074e1f4
Source dataset
uspto-grants-1990_05
Patent number
US04925859

Reaction notes

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