Sodium Hydroxide → HCID 86602877, compound

HRID 852553Notes

Reaction equation

HRID 852553 reaction equation
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:13]=[C:12]([S:14][C:15](=[O:19])[N:16]([CH3:18])[CH3:17])[CH:11]=[C:6]([C:7]([O:9]C)=[O:8])[CH:5]=1.[OH-].[Na+]>C1COCC1>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:13]=[C:12]([S:14][C:15](=[O:19])[N:16]([CH3:17])[CH3:18])[CH:11]=[C:6]([C:7]([OH:9])=[O:8])[CH:5]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 10827839HCID 10827839, compound

Product 1

HCID 86602877HCID 86602877, compoundYield 79.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5-dimethylcarbamoylsulfanyl-isophthalic acid dimethyl ester (D56) (6 g, 20.2 mmol, 1 equiv) in THF (100 ml) at room temperature was added 2N aqueous NaOH solution (9.6 ml, 19.2 mmol, 0.95 equiv). The resulting mixture was stirred for 11 h and then partitioned between AcOEt and H2O. The two layers were separated and the aqueous phase extracted with AcOEt. After acidification to pH 1, the aqueous phase was extracted twice with AcOEt. The organic solution was dried over MgSO4 then concentrated in vacuo to give 5-dimethylcarbamoylsulfanyl-isophthalic acid monomethyl ester (D57) (4.54 g, 79%) as a white solid.

Workup

  1. custompartitioned between AcOEt and H2O
  2. customThe two layers were separated
  3. extractionthe aqueous phase extracted with AcOEt
  4. extractionAfter acidification to pH 1, the aqueous phase was extracted twice with AcOEt
  5. dry with materialThe organic solution was dried over MgSO4
  6. concentrationthen concentrated in vacuo

Sources & evidence

ORD record
ord-b040fc55b85a4ae181c48516b5f4f530
Source dataset
uspto-grants-2007_08
Patent number
US07253198B2

Reaction notes

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