Ammonia → HCID 20297259, compound

HRID 1389619Notes

Reaction equation

HRID 1389619 reaction equation
N.[NH2-].[Na+].[C:4]1([S:10][CH:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)[C:12]([OH:14])=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[CH3:28]I.Cl>C(OCC)C.O>[C:4]1([S:10][C:11]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[CH:16]=2)([CH3:28])[C:12]([OH:14])=[O:13])[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

8

Reactant 5

HCID 222AmmoniaHCID 313Hydrochloric AcidHCID 6328Methyl iodideHCID 24533Sodium amide2×HCID 20297261HCID 20297261, compound

Product 1

HCID 20297259HCID 20297259, compoundYield 96.7%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
-40 °C

Procedure

15 ml of liquid ammonia was charged into a 50 ml flask and 0.2 g (8.7 mmols) of sodium metal was dissolved therein in the presence of a catalytic amount of ferric nitrate thereby forming a liquid ammonia suspension of sodium amide. Thereafter, 1.22 g (3.63 mmols) of 2-phenylthio-2-(3-phenoxyphenyl)acetic acid prepared as described in Example 1 dissolved in 10 ml of diethyl ether was added dropwise to the above suspension of sodium amide. The reaction mixture was then stirred for 30 minutes at a temperature of -40° C. and a solution of 0.75 g (5.3 mmols) of methyl iodide in 5 ml of diethyl ether was added to the reaction mixture which was then stirred for further 30 minutes at -40° C. The reaction mixture was then allowed to warm slowly by removing the cooling bath used and finally heated while refluxing for 15 minutes to complete the reaction. 30 ml of water was added to the reaction mixture to dissolve any solid substances and the mixture was rendered acidic with 1 N hydrochloric acid followed by being extracted with diethyl ether. The etherial extract was dried over anhydrous sodium sulfate and concentrated to obtain 1.23 g of a crude 2-phenylthio-2-(3-phenoxyphenyl)propionic acid. The resulting crude product was then purified by silica gel column chromatography eluting with diethyl ether-hexane (1:5 by volume) to obtain 1.10 g (87% yield) of the above product in a substantially pure form.

Workup

  1. stirringwas then stirred for further 30 minutes at -40° C
  2. temperatureto warm slowly
  3. customby removing the cooling bath
  4. temperaturefinally heated
  5. temperaturewhile refluxing for 15 minutes
  6. customthe reaction
  7. dissolutionto dissolve any solid substances
  8. extractionby being extracted with diethyl ether
  9. extractionThe etherial extract
  10. dry with materialwas dried over anhydrous sodium sulfate
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-c69d6c5e76be41a4ac4621faa79b8fa2
Source dataset
uspto-grants-1981_01
Patent number
US04245108

Reaction notes

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