Ammonia → HCID 14820088, compound

HRID 2166388Notes

Reaction equation

HRID 2166388 reaction equation
[NH3:1].[C:2]([C:5]1[C:19]([OH:20])=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15](Cl)=[O:16])=[C:7]([CH2:21][CH:22]=[CH2:23])[CH:6]=1)(=[O:4])[CH3:3]>C(Cl)Cl>[C:2]([C:5]1[C:19]([OH:20])=[CH:18][C:8]([O:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][C:15]([NH2:1])=[O:16])=[C:7]([CH2:21][CH:22]=[CH2:23])[CH:6]=1)(=[O:4])[CH3:3]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 15747283HCID 15747283, compound

Product 1

HCID 14820088HCID 14820088, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Ammonia gas was bubbled into a solution of approximately 3 millimoles of the acid chloride from Example 95 in 25 ml of methylene chloride. After 10 minutes, gas introduction was discontinued and the reaction was stirred overnight. The reaction mixture was concentrated in vacuo and then partitioned between ethyl acetate and dilute hydrochloric acid to which sodium chloride had been added. The organic layer was separated, washed with a potassium carbonate solution, dried over sodium sulfate, and concentrated to dryness. The residue was purified by preparative thin layer chromatography eluting with ethyl acetate to provide 110 mg of the desired title product, m.p.=122°-124° C.

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. custompartitioned between ethyl acetate and dilute hydrochloric acid to which sodium chloride
  3. additionhad been added
  4. customThe organic layer was separated
  5. washwashed with a potassium carbonate solution
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated to dryness
  8. customThe residue was purified by preparative thin layer chromatography
  9. washeluting with ethyl acetate

Sources & evidence

ORD record
ord-f3cf6597fc414cb6b5ab09016c96f485
Source dataset
uspto-grants-1990_07
Patent number
US04945099

Reaction notes

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