Sodium Iodide → HCID 13911228, compound

HRID 247471

Reaction equation

HRID 247471 reaction equation
[C:1]([C:5]1[C:9]([NH:10][C:11]([NH:13][CH2:14][CH2:15]Cl)=[O:12])=[CH:8][S:7][CH:6]=1)([O:3]C)=O.Cl.[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][NH:29][CH2:28][CH2:27]1.C(=O)(O)[O-].[Na+].[I-].[Na+].[OH-].[Na+]>O1CCCC1>[CH3:18][O:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[N:26]1[CH2:31][CH2:30][N:29]([CH2:15][CH2:14][N:13]2[C:1](=[O:3])[C:5]3=[CH:6][S:7][CH:8]=[C:9]3[NH:10][C:11]2=[O:12])[CH2:28][CH2:27]1

Participants

7

Reactant 5

HCID 5238Sodium IodideHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 9899402N-(2-Methoxyphenyl)piperazine hydrochlorideHCID 13911227HCID 13911227, compound

Product 1

HCID 13911228HCID 13911228, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A 500 ml tetrahydrofuran mixture containing 13.1 g (50 mmol) of N-(3-carbomethoxythien-4-yl)-N'-(2-chloroethyl)urea from (a), 35 g (150 mmol) of 1-(2-methoxyphenyl)piperazine hydrochloride, 21 g (250 mmol) of sodium bicarbonate and 3.75 g (25 mmol) of sodium iodide was heated to reflux under nitrogen for 4 days. The tetrahydrofuran was removed in vacuo and the residue was partitioned between H2O and CH2Cl2. The CH2Cl2 extracts were dried over MgSO4 and evaporated to dryness. This residue which contained the title compound of Example 2 was dissolved in 300 ml of methanol and treated with 4.5 g (56 mmol) of 50% NaOH. After the solution had been stirred at room temperature for 16 hours, the resulting precipitate was collected by filtration to afford 9.7 g of the title compound. The filtrate was purified by flash silica gel chromatography using 1-5% MeOH in CH2Cl2. There was obtained an additional 3.4 g of the title compound (13.1 g total, 68%) which was converted to its hydrochloride salt with isopropanolic hydrogen chloride, 9.1 g, mp 273°-275° C. (dec).

Workup

  1. temperaturewas heated
  2. temperatureto reflux under nitrogen for 4 days
  3. customThe tetrahydrofuran was removed in vacuo
  4. customthe residue was partitioned between H2O and CH2Cl2
  5. dry with materialThe CH2Cl2 extracts were dried over MgSO4
  6. customevaporated to dryness
  7. dissolutionwas dissolved in 300 ml of methanol
  8. filtrationthe resulting precipitate was collected by filtration

Sources & evidence

ORD record
ord-cd4056b9d58547288e68a0d57de1a1fd
Source dataset
uspto-grants-1987_11
Patent number
US04707550

Linked notes

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