Diethyl Ether → HCID 12674600, compound

HRID 596466Notes

Reaction equation

HRID 596466 reaction equation
C([O:3][C:4](=O)[CH:5]([NH:7][CH:8]([C:10](=O)[NH:11][C:12]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=1)[CH3:9])[CH3:6])C.C(OCC)C.[H-].[H-].[H-].[H-].[Li+].[Al+3]>O>[Cl:18][C:15]1[CH:14]=[CH:13][C:12]([NH:11][CH2:10][CH:8]([NH:7][CH:5]([CH3:6])[CH2:4][OH:3])[CH3:9])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 3283Diethyl Ether2×HCID 12674598HCID 12674598, compoundHCID 21226445Aluminium lithium hydride

Product 1

HCID 12674600HCID 12674600, compoundYield 98.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

95 Grams of 2-[1-(p-chlorophenylcarbamyl)ethylamino]-propionic acid ethyl ester dissolved in 1200 ml. of anhydrous diethyl ether is gradually added under stirring to a suspension of 38 g. of LiAlH4 in 2000 ml. of diethyl ether cooled to 0° C. The reaction mixture is refluxed for two hours with stirring, then the reaction complex is decomposed at 0° C. with water, stirred for 30 minutes at room temperature and the inorganic solids separated by filtration. The ether solution is dried and evaporated, and the residue, distilled in a bulb, yields 76 g. of the title compound. B.p. 170° C./0.4 mm Hg. yield 98.5%. The corresponding acetate, obtained by treatment of the title compound with acetyl chloride in acetic acid, boils at 160° C./0.5 mm Hg. In the same way, the corresponding m-chlorophenyl-substituted derivative is synthesized. B.p 170° C./0.5 mm Hg. The corresponding acetate boils at 160° C./0.5 mm Hg.

Workup

  1. temperatureThe reaction mixture is refluxed for two hours
  2. stirringwith stirring
  3. stirringstirred for 30 minutes at room temperature
  4. customthe inorganic solids separated by filtration
  5. dry with materialThe ether solution is dried
  6. customevaporated
  7. distillationthe residue, distilled in a bulb
  8. customyields 76 g

Sources & evidence

ORD record
ord-89aafe57fd044742a33dd68dbc29c62d
Source dataset
uspto-grants-1977_03
Patent number
US04011238

Reaction notes

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