Hydrochloric Acid → HCID 54555404, compound

HRID 2287368Notes

Reaction equation

HRID 2287368 reaction equation
[Na].Cl[C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36].Cl>C(O)CO>[OH:28][CH2:29][CH2:30][O:35][C:3]1[N:8]=[C:7]([C:9]2[N:14]=[CH:13][CH:12]=[CH:11][N:10]=2)[N:6]=[C:5]([NH:15][S:16]([CH:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([CH3:27])[CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=1[O:35][CH3:36]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 54065582HCID 54065582, compound

Product 1

HCID 54555404HCID 54555404, compoundYield 145%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Sodium (315 mg) was dissolved in 7.7 ml of ethylene glycol and 700 mg of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-(3-methylphenyl)ethenesulfonamide was added thereto with stirring. The reaction mixture was stirred at 90° C. for 30 minutes and poured into a mixture of 1N hydrochloric acid and ice. Crystals separated out therefrom were collected by filtration and the resulting crystals were purified by a silica gel column chromatography (chloroform-methanol=20:1). The resulting amorphous substance was crystallized in ether and collected filtration to give 533 mg of N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-(3-methylphenyl)ethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at 90° C. for 30 minutes
  2. customCrystals separated out
  3. filtrationtherefrom were collected by filtration
  4. customthe resulting crystals were purified by a silica gel column chromatography (chloroform-methanol=20:1)
  5. customThe resulting amorphous substance was crystallized in ether
  6. customcollected
  7. filtrationfiltration

Sources & evidence

ORD record
ord-f41a110f9d004e0b98cb8a067b24c759
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

Loading…