Sodium Chloride → HCID 14098085, compound

HRID 330012Notes

Reaction equation

HRID 330012 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.O[CH:33]([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][C:41]=1[O:46][CH3:47])[CH2:34][N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1.[SH:48][C:49]1[CH:58]=[CH:57][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:51][CH:50]=1.[Cl-].[Na+]>O1CCCC1>[CH3:47][O:46][C:41]1[CH:42]=[CH:43][CH:44]=[CH:45][C:40]=1[CH:33]([S:48][C:49]1[CH:50]=[CH:51][C:52]([C:53]([O:55][CH3:56])=[O:54])=[CH:57][CH:58]=1)[CH2:34][N:35]1[CH:39]=[CH:38][N:37]=[CH:36]1

Participants

7

Reactant 5

HCID 5234Sodium ChlorideHCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 237573Methyl 4-sulfanylbenzoateHCID 15055905HCID 15055905, compound

Product 1

HCID 14098085HCID 14098085, compoundYield 23.2%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

685 mg of triphenylphosphine were added, at a temperature between 0° and 5° C., to a solution of 500 mg of diethyl azodicarboxylate in 6.17 ml of tetrahydrofuran, and the mixture was stirred for 20 minutes. A solution of 570 mg of 1-[2-hydroxy-2-(2-methoxyphenyl)ethyl]imidazole in 7 ml of tetrahydrofuran was added to the resulting solution at a temperature between -10° and -15° C., and the mixture was stirred for 20 minutes. A solution of 439 mg of methyl 4-mercaptobenzoate in 8.4 ml of tetrahydrofuran was added at the same temperature to the mixture, which was then stirred at between 0° and 5° C. for 30 minutes, and then at room temperature for 25 minutes. A saturated aqueous solution of sodium chloride was added, and the reaction mixture was extracted with ethyl acetate. The extract was washed with water and then dried over anhydrous magnesium sulfate. The solvent was removed by distillation, and the residue was purified by the same method as described in Example 13, to give 223 mg of the title compound. This compound was identical with that obtained as described in Example 9 in its infrared absorption spectrum and nuclear magnetic resonance spectrum.

Workup

  1. stirringthe mixture was stirred for 20 minutes
  2. stirringwas then stirred at between 0° and 5° C. for 30 minutes
  3. waitat room temperature for 25 minutes
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe solvent was removed by distillation
  8. customthe residue was purified by the same method

Sources & evidence

ORD record
ord-a54460c11b59452cb69dd78059f5117f
Source dataset
uspto-grants-1990_01
Patent number
US04894385

Reaction notes

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