Sodium Hydroxide → HCID 178464626, compound

HRID 463779Notes

Reaction equation

HRID 463779 reaction equation
[OH-].[Na+].S(O)(O)(=O)=O.[CH2:8]([NH:10][C:11]([NH2:13])=[NH:12])[CH3:9].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([Cl:28])[C:23]=1[CH2:29][C:30](Cl)=[O:31]>O1CCCC1>[ClH:21].[CH2:8]([NH:10][C:11]([NH:13][C:30](=[O:31])[CH2:29][C:23]1[C:22]([Cl:21])=[CH:27][CH:26]=[CH:25][C:24]=1[Cl:28])=[NH:12])[CH3:9]

Participants

6

Reactant 4

HCID 14798Sodium HydroxideHCID 24436Sodium SulfateHCID 27581482-(2,6-Dichlorophenyl)acetyl chlorideHCID 178464632HCID 178464632, compound

Product 1

HCID 178464626HCID 178464626, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A mixture of 30.4 g of a 50% aqueous sodium hydroxide solution, 51.74 g of ethylguanidine sulfate and 800 ml of tetrahydrofuran is stirred for 45 minutes at RT. 60 g of anhydrous sodium sulfate are added and stirring continued for 45 minutes. A solution of 2,6-dichlorophenylacetyl chloride (41.69 g) in 200 ml of tetrahydrofuran is added dropwise and the reaction mixture stirred another day, filtered and concentrated in vacuo. The resulting yellow oil is partitioned between 250 ml of methylene chloride and 250 ml of H2O. After separating the two layers, the aqueous portion is extracted with methylene chloride, the combined organic extract dried over magnesium sulfate, filtered and acidified with hydrochloric acid/methanol. The acidified solution is concentrated in vacuo to afford a white solid which is recrystallized from acetonitrile/methanol affording a white solid, M.P. 228°-230° C.

Workup

  1. stirringstirring
  2. waitcontinued for 45 minutes
  3. stirringthe reaction mixture stirred another day
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe resulting yellow oil is partitioned between 250 ml of methylene chloride and 250 ml of H2O
  7. customAfter separating the two layers
  8. extractionthe aqueous portion is extracted with methylene chloride
  9. extractionthe combined organic extract
  10. dry with materialdried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationThe acidified solution is concentrated in vacuo
  13. customto afford a white solid which
  14. customis recrystallized from acetonitrile/methanol affording a white solid, M.P. 228°-230° C.

Sources & evidence

ORD record
ord-304c0164494d494f89e451f1df801f6b
Source dataset
uspto-grants-1985_10
Patent number
US04544670

Reaction notes

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