Ethylene Glycol → HCID 19735392, compound

HRID 326712

Reaction equation

HRID 326712 reaction equation
Cl[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][C:24](OC)=[CH:23][CH:22]=1.[C:29]([O-:33])(=O)[CH2:30][OH:31].[Na+].[Na].C(O)[CH2:37][OH:38]>>[OH:31][CH2:30][CH2:29][O:33][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][S:9]([C:12]2[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=2)(=[O:11])=[O:10])[C:3]=1[CH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=1[O:38][CH3:37]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 517347Sodium GlycolateHCID 5360545SodiumHCID 12396954HCID 12396954, compound

Product 1

HCID 19735392HCID 19735392, compound

Conditions

Temperature
125 °C

Procedure

300 mg of N-[6-chloro-5-(p-methoxybenzyl)-4-pyrimidinyl]-p-methoxybenzenesulfonamide were added to a sodium glycolate solution from 1 ml of dry ethylene glycol and 46 mg of sodium. The reaction mixture was heated at 125° C. for 4 hours under an argon atmosphere. Thereafter, the ethylene glycol was distilled under reduced pressure. The residue was partitioned between ethyl acetate and 1N hydrochloric acid. The organic phase was washed neutral, dried and evaporated. The residue was chromatographed on silica gel with methylene chloride/ethyl acetate (1:1 v/v). There were obtained 250 mg of N-[6-(2-hydroxyethoxy)-5-(o-methoxybenzyl)-4-pyrimidinyl]-p-methoxybenzenesulfonamide, melting point 161°-162° C.

Workup

  1. distillationThereafter, the ethylene glycol was distilled under reduced pressure
  2. customThe residue was partitioned between ethyl acetate and 1N hydrochloric acid
  3. washThe organic phase was washed neutral
  4. customdried
  5. customevaporated
  6. customThe residue was chromatographed on silica gel with methylene chloride/ethyl acetate (1:1 v/v)

Sources & evidence

ORD record
ord-e0b87538e9714a53aab5aecb6702ad63
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Linked notes

Loading…