Ammonium Chloride → HCID 18322224, compound

HRID 1698846Notes

Reaction equation

HRID 1698846 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH2:9][CH2:10][N:11]2[C:15](=[O:16])[C:14]3=[CH:17][CH:18]=[CH:19][CH:20]=[C:13]3[C:12]2=[O:21])[CH:6]=[CH:7][CH:8]=1.[S:22]1[CH:26]=[CH:25][CH:24]=[C:23]1[Li].[Cl-].[NH4+]>O1CCCC1>[OH:21][C:12]1([C:23]2[S:22][CH:26]=[CH:25][CH:24]=2)[C:13]2[C:14](=[CH:17][CH:18]=[CH:19][CH:20]=2)[C:15](=[O:16])[N:11]1[CH2:10][CH2:9][C:5]1[CH:6]=[CH:7][CH:8]=[C:3]([O:2][CH3:1])[CH:4]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 18322222HCID 18322222, compoundHCID 178418439HCID 178418439, compound

Product 1

HCID 18322224HCID 18322224, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.3 g (1.07 mmol) of N-(2-(3-methoxyphenyl)ethyl)phthalimide was dissolved in 10 ml of absolute tetrahydrofuran and, at 0° C., admixed dropwise with a 1 M solution of 0.14 g (1.6 mmol) of 2-thienyllithium. The reaction mixture was allowed to warm to room temperature, after which stirring was continued for 2 h, and the mixture was then admixed with 10 ml of saturated ammonium chloride solution. The mixture was extracted three times with diethyl ether and the combined organic phases were washed once with saturated sodium chloride solution, dried and evaporated to dryness using a rotary evaporator. The oily crude product was purified by chromatography. Elution was carried out using a dichloromethanelmethanol gradient (0 to 1% methanol). Yield: 0.2 g of an oil.

Workup

  1. extractionThe mixture was extracted three times with diethyl ether
  2. washthe combined organic phases were washed once with saturated sodium chloride solution
  3. customdried
  4. customevaporated to dryness
  5. customa rotary evaporator
  6. customThe oily crude product was purified by chromatography
  7. washElution

Sources & evidence

ORD record
ord-9c49dd5f3de940a9a484162aea94af2b
Source dataset
uspto-grants-2002_02
Patent number
US06344468B1

Reaction notes

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