Hydrochloric Acid → HCID 53826330, compound

HRID 2287361Notes

Reaction equation

HRID 2287361 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]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35].Cl>C(O)CO>[OH:27][CH2:28][CH2:29][O:34][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]=[CH:23][CH:22]=2)(=[O:18])=[O:17])[C:4]=1[O:27][C:28]1[CH:33]=[CH:32][CH:31]=[CH:30][C:29]=1[O:34][CH3:35]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 5360545SodiumHCID 53744388N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide

Product 1

HCID 53826330HCID 53826330, compoundYield 192.1%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Procedure

Sodium (230 mg) was dissolved in 5.6 ml of ethylene glycol and 495 mg of N-[6-chloro-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide was added thereto under ice cooling with stirring. The reaction mixture was stirred at 80° C. for three hours and poured into a mixture of 1N hydrochloric acid and ice. The crystals separated out therefrom were collected by filtration and the resulting crystals were purified by a silica gel column chromatography (chloroform-methanol=20:1) to give 500 mg of N-[6-(2-hydroxyethoxy)-5-(2-methoxyphenoxy)-2-(2-pyrimidinyl)-4-pyrimidinyl]-2-phenylethenesulfonamide.

Workup

  1. stirringThe reaction mixture was stirred at 80° C. for three hours
  2. customThe crystals separated out
  3. filtrationtherefrom were collected by filtration
  4. customthe resulting crystals were purified by a silica gel column chromatography (chloroform-methanol=20:1)

Sources & evidence

ORD record
ord-16683df5ffdd42f7a3f54050a3d31d64
Source dataset
uspto-grants-2000_07
Patent number
US06083955

Reaction notes

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