Ammonia → HCID 23047741, compound

HRID 2107147Notes

Reaction equation

HRID 2107147 reaction equation
[NH3:1].Cl[C:3]([CH:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:4]>C(Cl)Cl>[NH2:1][C:3]([CH:5]([CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1)[C:6]([O:8][CH2:9][CH3:10])=[O:7])=[O:4]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 23047721HCID 23047721, compound

Product 1

HCID 23047741HCID 23047741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A saturated solution of gaseous ammonia in 25 ml of methylene chloride is added drop by drop at -10° C. to a solution of 5.6 (17 mmol) of ethyl 2-(chlorocarbonyl)-7-(4-chlorophenyl)heptanoate in 50 ml of methylene chloride. The mixture is stirred for 30 minutes at room temperature, suction filtered from the ammonium chloride, the filtrate is washed with water, and dried and concentrated. The concentrate is chromatographed on silica gel with a mixture of toluene and dioxane (5:1). 3.6 g (68% of theory) is obtained of ethyl 2-(aminocarbonyl)-7-(4-chlorophenyl)heptanoate, M.P. 110°-111° C.

Workup

  1. filtrationsuction filtered from the ammonium chloride
  2. washthe filtrate is washed with water
  3. customdried
  4. concentrationconcentrated
  5. customThe concentrate is chromatographed on silica gel with a mixture of toluene and dioxane (5:1)

Sources & evidence

ORD record
ord-f8378a0353fb4b69b3024e2568fc3b7f
Source dataset
uspto-grants-1990_06
Patent number
US04933367

Reaction notes

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