Hydrochloric Acid → 4-tert-butyl-N-{6-(2-hydroxyethylthio)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide

HRID 1082269Notes

Reaction equation

HRID 1082269 reaction equation
[SH:1][CH2:2][CH2:3][OH:4].[H-].[Na+].[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]2[C:26]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)=[C:25](Cl)[N:24]=[CH:23][N:22]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8].Cl>CC(N(C)C)=O>[C:7]([C:11]1[CH:16]=[CH:15][C:14]([S:17]([NH:20][C:21]2[C:26]([O:27][C:28]3[CH:33]=[CH:32][CH:31]=[C:30]([O:34][CH3:35])[CH:29]=3)=[C:25]([S:1][CH2:2][CH2:3][OH:4])[N:24]=[CH:23][N:22]=2)(=[O:19])=[O:18])=[CH:13][CH:12]=1)([CH3:10])([CH3:9])[CH3:8]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 15672-MercaptoethanolHCID 24758Sodium hydrideHCID 15391273p-t-butyl-N-[6-chloro-5-(m-methoxyphenoxy)-4-pyrimidinyl]benzenesulfonamide

Product 1

HCID 117626924-tert-butyl-N-{6-(2-hydroxyethylthio)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamideYield 69.5%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-mercaptoethanol (1.31 g) in dimethylacetamide (15 ml) is added sodium hydride (62.3% dispersion-type, 520 mg) under argon atmosphere. Five minutes later, to the mixture is added 4-tert-butyl-N-{6-chloro-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (1.5 g), and the mixture is reacted under argon atmosphere at 70° C. for two hours, at 100° C. for three hours, and further reacted at 130° C. for two hours. The reaction solution is treated with hydrochloric acid, and extracted with ethyl acetate. The ethyl acetate layer is washed, dried, and evaporated to remove the solvent. The residue is purified by silica gel column chromatography (solvent; chloroform/methanol=70:1), and recrystallized from ethyl acetate/n-hexane to give 4-tert-butyl-N-{6-(2-hydroxyethylthio)-5-(3-methoxyphenoxy)pyrimidin-4-yl}benzenesulfonamide (1.14 g) as crystals.

Workup

  1. customthe mixture is reacted under argon atmosphere at 70° C. for two hours, at 100° C. for three hours
  2. customfurther reacted at 130° C. for two hours
  3. extractionextracted with ethyl acetate
  4. washThe ethyl acetate layer is washed
  5. customdried
  6. customevaporated
  7. customto remove the solvent
  8. customThe residue is purified by silica gel column chromatography (solvent; chloroform/methanol=70:1)
  9. customrecrystallized from ethyl acetate/n-hexane

Sources & evidence

ORD record
ord-7bfdf44ea21d473ab476f66f2d2d2ff9
Source dataset
uspto-grants-1996_12
Patent number
US05589478

Reaction notes

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