Sodium Glycolate → HCID 10983585, compound

HRID 486636

Reaction equation

HRID 486636 reaction equation
[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19](Cl)[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].[C:31]([O-])(=[O:34])[CH2:32][OH:33].[Na+].[Na]>C(O)CO>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([S:11]([NH:14][C:15]2[C:20]([O:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=3[O:28][CH3:29])=[C:19]([O:33][CH2:32][CH2:31][OH:34])[N:18]=[CH:17][N:16]=2)(=[O:13])=[O:12])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 517347Sodium GlycolateHCID 5360545SodiumHCID 15819129HCID 15819129, compound

Product 1

HCID 10983585HCID 10983585, compound

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
95 °C

Procedure

886 mg of p-t-butyl-N-[6-chloro-5-(o-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide were added to a sodium glycolate solution from 3.0 g of ethylene glycol and 138 mg of sodium. The reaction mixture was stirred at 95° C. under argon for 4 hours. Thereafter, the ethylene glycol was distilled off and the residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase was dried and the solvent was distilled off. The residue was crystallized from diisopropyl ether. There were obtained 870 mg of p-t-butyl-N-[6-(2-hydroxyethoxy)-5-(o-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide. M.p. 143°-148° C.

Workup

  1. distillationThereafter, the ethylene glycol was distilled off
  2. customthe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. customThe organic phase was dried
  4. distillationthe solvent was distilled off
  5. customThe residue was crystallized from diisopropyl ether

Sources & evidence

ORD record
ord-b360a1b4b98848529920094915422e2f
Source dataset
uspto-grants-1994_03
Patent number
US05292740

Linked notes

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