Ethylene Glycol → HCID 19735343, compound

HRID 326693Notes

Reaction equation

HRID 326693 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]([C:18]([F:21])([F:20])[F:19])=[CH:14][CH:13]=2)(=[O:11])=[O:10])[C:3]=1[C:22]1[CH:27]=[CH:26][C:25]([Cl:28])=[CH:24][CH:23]=1.Cl.[CH2:30]([OH:33])[CH2:31][OH:32]>C(OCC)(=O)C>[Cl:28][C:25]1[CH:26]=[CH:27][C:22]([C:3]2[C:4]([NH:8][S:9]([C:12]3[CH:13]=[CH:14][C:15]([C:18]([F:19])([F:20])[F:21])=[CH:16][CH:17]=3)(=[O:10])=[O:11])=[N:5][CH:6]=[N:7][C:2]=2[O:32][CH2:31][CH2:30][OH:33])=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 174Ethylene GlycolHCID 313Hydrochloric AcidHCID 19735307HCID 19735307, compound

Product 1

HCID 19735343HCID 19735343, compound

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 0.046 g of Na in 1.5 ml of absolute ethylene glycol was treated with 0.216 g of N-[6-chloro-5-(p-chloro-phenyl)-4-pyrimidinyl]-α,α,α-trifluoro-p-toluenesulfonamide with the exclusion of moisture and heated at 100° C. for 3 hours, thereafter cooled to room temperature and treated with 2.3 ml of 1N HCl. The mixture was taken up in ethyl acetate, the organic extracts were washed with water, dried and evaporated under reduced pressure. The precipitate remaining behind was recrystallized from CH2Cl2, isopropyl ether and n-hexane and yielded N-[5-(p-chlorophenyl)-6-(2-hydroxyethoxy)-4-pyrimidinyl]-α,α,α-trifluoro-p-toluenesulfonamide, melting point 160°-162° C.

Workup

  1. temperaturecooled to room temperature
  2. washthe organic extracts were washed with water
  3. customdried
  4. customevaporated under reduced pressure
  5. customThe precipitate remaining behind was recrystallized from CH2Cl2, isopropyl ether and n-hexane

Sources & evidence

ORD record
ord-5968a1e09c914b909b7e6681df5104ec
Source dataset
uspto-grants-1993_12
Patent number
US05270313

Reaction notes

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