Ethylene Glycol → 4-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide

HRID 1082304

Reaction equation

HRID 1082304 reaction equation
[H-].[Na+].[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[CH:22]=[C:21](Cl)[N:20]=[CH:19][N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4].Cl.[CH2:25]([OH:28])[CH2:26][OH:27]>>[C:3]([C:7]1[CH:12]=[CH:11][C:10]([S:13]([NH:16][C:17]2[CH:22]=[C:21]([O:27][CH2:26][CH2:25][OH:28])[N:20]=[CH:19][N:18]=2)(=[O:15])=[O:14])=[CH:9][CH:8]=1)([CH3:6])([CH3:5])[CH3:4]

Participants

5

Reactant 4

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 24758Sodium hydrideHCID 108710784-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide

Product 1

HCID 117831024-tert-butyl-N-[6-(2-hydroxyethoxy)pyrimidin-4-yl)benzenesulfonamide

Conditions

Temperature
60 °C

Procedure

To ethylene glycol (20 ml) is added sodium hydride (60% dispersion-type, 1.03 g), and thereto is added 4-tert-butyl-N-(6-chloropyrimidin-4-yl)benzenesulfonamide (1.66 g). The mixture is stirred at 60° C. for 20 hours. After cooling, the mixture is acidified with 10% hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is crystallized from ethyl acetate to give 4-tertbutyl-N-{6-(2-hydroxyethoxy)pyrimidin-4-yl}benzenesulfonamide (1.58 g).

Workup

  1. temperatureAfter cooling
  2. extractionextracted with ethyl acetate
  3. washThe ethyl acetate layer is washed
  4. customdried
  5. customevaporated
  6. customto remove the solvent
  7. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b095e8034f534f03b0ee7f96f8694aa7
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Linked notes

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